GB1578963A - Cyclic esters of 3,4-dihydroxy-thiophene-1,1-dioxide compounds and 3,4-dihydroxy-cyclopentadienone compounds and their use as intermediates - Google Patents
Cyclic esters of 3,4-dihydroxy-thiophene-1,1-dioxide compounds and 3,4-dihydroxy-cyclopentadienone compounds and their use as intermediates Download PDFInfo
- Publication number
- GB1578963A GB1578963A GB23381/77A GB2338177A GB1578963A GB 1578963 A GB1578963 A GB 1578963A GB 23381/77 A GB23381/77 A GB 23381/77A GB 2338177 A GB2338177 A GB 2338177A GB 1578963 A GB1578963 A GB 1578963A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dioxide
- yield
- solution
- melting point
- added
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
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- 239000000543 intermediate Substances 0.000 title claims description 10
- 125000004122 cyclic group Chemical group 0.000 title claims description 9
- UJOIYDLLLBKIJL-UHFFFAOYSA-N 3,4-dihydroxycyclopenta-2,4-dien-1-one Chemical class OC1=CC(=O)C=C1O UJOIYDLLLBKIJL-UHFFFAOYSA-N 0.000 title description 2
- KGCBGYIFCPRLHC-UHFFFAOYSA-N 1,1-dioxothiophene-3,4-diol Chemical class OC1=CS(=O)(=O)C=C1O KGCBGYIFCPRLHC-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 53
- 150000002148 esters Chemical class 0.000 claims description 49
- -1 amine hydrochloride Chemical class 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 34
- 230000008569 process Effects 0.000 claims description 23
- 238000004519 manufacturing process Methods 0.000 claims description 16
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 6
- 239000000010 aprotic solvent Substances 0.000 claims description 5
- DISFUWHHERKHDM-UHFFFAOYSA-N OC=1C(O)=C(C=2C=CC=CC=2)C(=O)C=1C1=CC=CC=C1 Chemical compound OC=1C(O)=C(C=2C=CC=CC=2)C(=O)C=1C1=CC=CC=C1 DISFUWHHERKHDM-UHFFFAOYSA-N 0.000 claims description 3
- HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical compound OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 claims description 3
- 235000006408 oxalic acid Nutrition 0.000 claims description 3
- LBPBCSAVVYSSJM-UHFFFAOYSA-N 2,5-diphenylthiophene-3,4-diol Chemical compound OC=1C(O)=C(C=2C=CC=CC=2)SC=1C1=CC=CC=C1 LBPBCSAVVYSSJM-UHFFFAOYSA-N 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 114
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 70
- 238000002844 melting Methods 0.000 claims 62
- 230000008018 melting Effects 0.000 claims 62
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 60
- 239000000203 mixture Substances 0.000 claims 52
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 50
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 47
- 238000006243 chemical reaction Methods 0.000 claims 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 43
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 36
- 238000010992 reflux Methods 0.000 claims 35
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 34
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 33
- 229920005989 resin Polymers 0.000 claims 33
- 239000011347 resin Substances 0.000 claims 33
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 24
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 21
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims 21
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 20
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 17
- 239000002904 solvent Substances 0.000 claims 16
- 238000009835 boiling Methods 0.000 claims 15
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 15
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 14
- 239000003208 petroleum Substances 0.000 claims 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 13
- 239000000047 product Substances 0.000 claims 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 12
- 229960000583 acetic acid Drugs 0.000 claims 12
- 150000001412 amines Chemical class 0.000 claims 12
- 239000012362 glacial acetic acid Substances 0.000 claims 12
- 238000001953 recrystallisation Methods 0.000 claims 12
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims 11
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 claims 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 10
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims 10
- 239000000706 filtrate Substances 0.000 claims 10
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims 10
- 235000019341 magnesium sulphate Nutrition 0.000 claims 10
- 230000000269 nucleophilic effect Effects 0.000 claims 10
- 229920000642 polymer Polymers 0.000 claims 10
- 238000002360 preparation method Methods 0.000 claims 10
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 claims 9
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims 9
- 238000003786 synthesis reaction Methods 0.000 claims 9
- CANZBRDGRHNSGZ-NSHDSACASA-N (2s)-3-methyl-2-(phenylmethoxycarbonylamino)butanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC(=O)OCC1=CC=CC=C1 CANZBRDGRHNSGZ-NSHDSACASA-N 0.000 claims 8
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 8
- 239000002253 acid Substances 0.000 claims 8
- 230000015572 biosynthetic process Effects 0.000 claims 8
- 230000008030 elimination Effects 0.000 claims 8
- 238000003379 elimination reaction Methods 0.000 claims 8
- 108090000765 processed proteins & peptides Proteins 0.000 claims 8
- 150000003335 secondary amines Chemical class 0.000 claims 8
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 7
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 claims 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 7
- 239000012074 organic phase Substances 0.000 claims 7
- SZXBQTSZISFIAO-ZETCQYMHSA-N (2s)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC(=O)OC(C)(C)C SZXBQTSZISFIAO-ZETCQYMHSA-N 0.000 claims 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 6
- 150000001408 amides Chemical class 0.000 claims 6
- 229940024606 amino acid Drugs 0.000 claims 6
- 235000001014 amino acid Nutrition 0.000 claims 6
- 239000002585 base Substances 0.000 claims 6
- 238000001704 evaporation Methods 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims 6
- 239000007787 solid Substances 0.000 claims 6
- 150000003512 tertiary amines Chemical class 0.000 claims 6
- 150000003672 ureas Chemical class 0.000 claims 6
- YBFHILNBYXCJKD-UHFFFAOYSA-N 1-(6-methylpyridin-3-yl)-2-(4-methylsulfonylphenyl)ethanone Chemical compound C1=NC(C)=CC=C1C(=O)CC1=CC=C(S(C)(=O)=O)C=C1 YBFHILNBYXCJKD-UHFFFAOYSA-N 0.000 claims 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 5
- 108010016626 Dipeptides Proteins 0.000 claims 5
- 125000002252 acyl group Chemical group 0.000 claims 5
- 235000013877 carbamide Nutrition 0.000 claims 5
- 150000005676 cyclic carbonates Chemical class 0.000 claims 5
- 238000000354 decomposition reaction Methods 0.000 claims 5
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims 5
- 238000001035 drying Methods 0.000 claims 5
- 239000000843 powder Substances 0.000 claims 5
- 239000002244 precipitate Substances 0.000 claims 5
- 239000011541 reaction mixture Substances 0.000 claims 5
- 239000007858 starting material Substances 0.000 claims 5
- 238000003756 stirring Methods 0.000 claims 5
- ZFJBSYYIOPSWAE-UHFFFAOYSA-N 1,1-diethyl-3-phenylurea Chemical compound CCN(CC)C(=O)NC1=CC=CC=C1 ZFJBSYYIOPSWAE-UHFFFAOYSA-N 0.000 claims 4
- QGLVWTFUWVTDEQ-UHFFFAOYSA-N 2-chloro-3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1Cl QGLVWTFUWVTDEQ-UHFFFAOYSA-N 0.000 claims 4
- HBAHZZVIEFRTEY-UHFFFAOYSA-N 2-heptylcyclohex-2-en-1-one Chemical compound CCCCCCCC1=CCCCC1=O HBAHZZVIEFRTEY-UHFFFAOYSA-N 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 229920001367 Merrifield resin Polymers 0.000 claims 4
- 238000005481 NMR spectroscopy Methods 0.000 claims 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 4
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 claims 4
- 239000004202 carbamide Substances 0.000 claims 4
- 239000012043 crude product Substances 0.000 claims 4
- 238000004821 distillation Methods 0.000 claims 4
- 238000002329 infrared spectrum Methods 0.000 claims 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims 4
- 239000012948 isocyanate Substances 0.000 claims 4
- 150000002513 isocyanates Chemical class 0.000 claims 4
- KUGLDBMQKZTXPW-JEDNCBNOSA-N methyl (2s)-2-amino-3-methylbutanoate;hydrochloride Chemical compound Cl.COC(=O)[C@@H](N)C(C)C KUGLDBMQKZTXPW-JEDNCBNOSA-N 0.000 claims 4
- 150000002923 oximes Chemical class 0.000 claims 4
- 229960005190 phenylalanine Drugs 0.000 claims 4
- 150000003141 primary amines Chemical class 0.000 claims 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 4
- JXGVXCZADZNAMJ-NSHDSACASA-N (2s)-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCN1C(=O)OCC1=CC=CC=C1 JXGVXCZADZNAMJ-NSHDSACASA-N 0.000 claims 3
- RTTPRNXQDFCDIY-UHFFFAOYSA-N 2-(dibenzylamino)-2-oxoacetic acid Chemical compound C=1C=CC=CC=1CN(C(=O)C(=O)O)CC1=CC=CC=C1 RTTPRNXQDFCDIY-UHFFFAOYSA-N 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims 3
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 3
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical class NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 claims 3
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 3
- 150000001298 alcohols Chemical class 0.000 claims 3
- WTINJQXJTHUFRF-YULYYXEXSA-N antamanide Chemical compound C([C@@H]1C(=O)N[C@H](C(N2CCC[C@H]2C(=O)N2CCC[C@H]2C(=O)N[C@@H](C)C(=O)N[C@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N2CCC[C@H]2C(=O)N2CCC[C@H]2C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N1)=O)C(C)C)C1=CC=CC=C1 WTINJQXJTHUFRF-YULYYXEXSA-N 0.000 claims 3
- 108010036237 antamanide Proteins 0.000 claims 3
- 230000008901 benefit Effects 0.000 claims 3
- 235000019445 benzyl alcohol Nutrition 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 238000006482 condensation reaction Methods 0.000 claims 3
- 238000002955 isolation Methods 0.000 claims 3
- DWKPPFQULDPWHX-VKHMYHEASA-N l-alanyl ester Chemical compound COC(=O)[C@H](C)N DWKPPFQULDPWHX-VKHMYHEASA-N 0.000 claims 3
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 150000002989 phenols Chemical class 0.000 claims 3
- 102000004196 processed proteins & peptides Human genes 0.000 claims 3
- 229960002429 proline Drugs 0.000 claims 3
- 230000009257 reactivity Effects 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 239000011593 sulfur Substances 0.000 claims 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims 3
- 238000012546 transfer Methods 0.000 claims 3
- 238000006276 transfer reaction Methods 0.000 claims 3
- ZYJPUMXJBDHSIF-NSHDSACASA-N (2s)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 ZYJPUMXJBDHSIF-NSHDSACASA-N 0.000 claims 2
- VMMKOEZGYYQVGX-UHFFFAOYSA-N 1,1-dioxo-2,5-diphenylthiophen-3-ol Chemical compound O=S1(=O)C(C=2C=CC=CC=2)=CC(O)=C1C1=CC=CC=C1 VMMKOEZGYYQVGX-UHFFFAOYSA-N 0.000 claims 2
- NZPSDGIEKAQVEZ-UHFFFAOYSA-N 1,3-benzodioxol-2-one Chemical compound C1=CC=CC2=C1OC(=O)O2 NZPSDGIEKAQVEZ-UHFFFAOYSA-N 0.000 claims 2
- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 2
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 claims 2
- JIJPQPVGZVIOMW-UHFFFAOYSA-N 4-hydroxy-2,5-diphenylthiophen-3-one Chemical compound O=C1C(O)=C(C=2C=CC=CC=2)SC1C1=CC=CC=C1 JIJPQPVGZVIOMW-UHFFFAOYSA-N 0.000 claims 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 2
- 230000004913 activation Effects 0.000 claims 2
- 238000004458 analytical method Methods 0.000 claims 2
- 150000008064 anhydrides Chemical class 0.000 claims 2
- 150000001450 anions Chemical class 0.000 claims 2
- 150000003934 aromatic aldehydes Chemical class 0.000 claims 2
- 239000011230 binding agent Substances 0.000 claims 2
- 239000004305 biphenyl Substances 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 2
- 230000000052 comparative effect Effects 0.000 claims 2
- ONCCWDRMOZMNSM-FBCQKBJTSA-N compound Z Chemical compound N1=C2C(=O)NC(N)=NC2=NC=C1C(=O)[C@H]1OP(O)(=O)OC[C@H]1O ONCCWDRMOZMNSM-FBCQKBJTSA-N 0.000 claims 2
- 238000001816 cooling Methods 0.000 claims 2
- 239000013078 crystal Substances 0.000 claims 2
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 claims 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims 2
- 238000001914 filtration Methods 0.000 claims 2
- 238000004817 gas chromatography Methods 0.000 claims 2
- 239000013067 intermediate product Substances 0.000 claims 2
- 229940035429 isobutyl alcohol Drugs 0.000 claims 2
- YDNLNVZZTACNJX-UHFFFAOYSA-N isocyanatomethylbenzene Chemical compound O=C=NCC1=CC=CC=C1 YDNLNVZZTACNJX-UHFFFAOYSA-N 0.000 claims 2
- CEMZBWPSKYISTN-YFKPBYRVSA-N methyl (2s)-2-amino-3-methylbutanoate Chemical compound COC(=O)[C@@H](N)C(C)C CEMZBWPSKYISTN-YFKPBYRVSA-N 0.000 claims 2
- 150000004702 methyl esters Chemical class 0.000 claims 2
- 150000002825 nitriles Chemical class 0.000 claims 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims 2
- 125000001209 o-nitrophenyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])[N+]([O-])=O 0.000 claims 2
- 230000003647 oxidation Effects 0.000 claims 2
- 238000007254 oxidation reaction Methods 0.000 claims 2
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 claims 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical class O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 2
- 230000035484 reaction time Effects 0.000 claims 2
- 238000012552 review Methods 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 2
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 2
- 150000003457 sulfones Chemical class 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims 2
- 150000003673 urethanes Chemical class 0.000 claims 2
- MRCKRGSNLOHYRA-UHFFFAOYSA-N (2-nitrophenyl) acetate Chemical group CC(=O)OC1=CC=CC=C1[N+]([O-])=O MRCKRGSNLOHYRA-UHFFFAOYSA-N 0.000 claims 1
- BYNFPGLZQXITMV-VWURTLBMSA-N (2s)-2-amino-3-phenylpropanoic acid;(2s)-2-aminopropanoic acid Chemical compound C[C@H](N)C(O)=O.OC(=O)[C@@H](N)CC1=CC=CC=C1 BYNFPGLZQXITMV-VWURTLBMSA-N 0.000 claims 1
- SSOAJNDTFAUPLS-UHFFFAOYSA-N (4-hydroxy-1,1-dioxo-2,5-diphenylthiophen-3-yl) n,n-diethylcarbamate Chemical compound O=S1(=O)C(C=2C=CC=CC=2)=C(O)C(OC(=O)N(CC)CC)=C1C1=CC=CC=C1 SSOAJNDTFAUPLS-UHFFFAOYSA-N 0.000 claims 1
- YBADLXQNJCMBKR-UHFFFAOYSA-M (4-nitrophenyl)acetate Chemical compound [O-]C(=O)CC1=CC=C([N+]([O-])=O)C=C1 YBADLXQNJCMBKR-UHFFFAOYSA-M 0.000 claims 1
- NPEHMGPRNCQEOS-UHFFFAOYSA-N 1,1-dioxo-2,5-diphenylthiophene-3,4-diol Chemical compound O=S1(=O)C(C=2C=CC=CC=2)=C(O)C(O)=C1C1=CC=CC=C1 NPEHMGPRNCQEOS-UHFFFAOYSA-N 0.000 claims 1
- XKAFKUGMXFMRCC-UHFFFAOYSA-N 1,1-diphenylurea Chemical compound C=1C=CC=CC=1N(C(=O)N)C1=CC=CC=C1 XKAFKUGMXFMRCC-UHFFFAOYSA-N 0.000 claims 1
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 claims 1
- WEERVPDNCOGWJF-UHFFFAOYSA-N 1,4-bis(ethenyl)benzene Chemical compound C=CC1=CC=C(C=C)C=C1 WEERVPDNCOGWJF-UHFFFAOYSA-N 0.000 claims 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 claims 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims 1
- XXFBRXQVPJVXFB-UHFFFAOYSA-N 1-benzyl-3-phenylurea Chemical compound C=1C=CC=CC=1NC(=O)NCC1=CC=CC=C1 XXFBRXQVPJVXFB-UHFFFAOYSA-N 0.000 claims 1
- GGCNUGIIDOOCMF-UHFFFAOYSA-N 1-benzylpiperidine-2-carboxamide Chemical compound NC(=O)C1CCCCN1CC1=CC=CC=C1 GGCNUGIIDOOCMF-UHFFFAOYSA-N 0.000 claims 1
- SQBHGDSDVWCPHN-UHFFFAOYSA-N 1-methyl-3-phenylurea Chemical compound CNC(=O)NC1=CC=CC=C1 SQBHGDSDVWCPHN-UHFFFAOYSA-N 0.000 claims 1
- VTLKOQYZSKCBQX-UHFFFAOYSA-N 2-[(4-fluorophenyl)carbamoyl-methylamino]oxyacetic acid Chemical compound OC(=O)CON(C)C(=O)NC1=CC=C(F)C=C1 VTLKOQYZSKCBQX-UHFFFAOYSA-N 0.000 claims 1
- SNQCHPCXUKRNCU-UHFFFAOYSA-N 3-benzyl-1,1-diethylurea Chemical compound CCN(CC)C(=O)NCC1=CC=CC=C1 SNQCHPCXUKRNCU-UHFFFAOYSA-N 0.000 claims 1
- OBGWBMNNRYZGNO-UHFFFAOYSA-N 4,5-diphenyl-2,3-dihydrothiophene 1,1-dioxide Chemical compound C1(=CC=CC=C1)C1=C(CCS1(=O)=O)C1=CC=CC=C1 OBGWBMNNRYZGNO-UHFFFAOYSA-N 0.000 claims 1
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 claims 1
- GJNGXPDXRVXSEH-UHFFFAOYSA-N 4-chlorobenzonitrile Chemical compound ClC1=CC=C(C#N)C=C1 GJNGXPDXRVXSEH-UHFFFAOYSA-N 0.000 claims 1
- ISSCDFCILPINAR-UHFFFAOYSA-N 4-hydroxy-1,1-dioxo-2,5-diphenylthiolan-3-one Chemical compound O=S1(=O)C(C=2C=CC=CC=2)C(=O)C(O)C1C1=CC=CC=C1 ISSCDFCILPINAR-UHFFFAOYSA-N 0.000 claims 1
- UIVWXNPUCAHAJX-UHFFFAOYSA-N 4-hydroxy-1,1-dioxo-2,5-diphenylthiophen-3-one Chemical compound O=S1(=O)C(C=2C=CC=CC=2)C(=O)C(O)=C1C1=CC=CC=C1 UIVWXNPUCAHAJX-UHFFFAOYSA-N 0.000 claims 1
- 235000001674 Agaricus brunnescens Nutrition 0.000 claims 1
- 241000948470 Amanita phalloides Species 0.000 claims 1
- DTCJYIIKPVRVDD-UHFFFAOYSA-N Benzthiazuron Chemical compound C1=CC=C2SC(NC(=O)NC)=NC2=C1 DTCJYIIKPVRVDD-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- DQZCVNGCTZLGAQ-UHFFFAOYSA-N Cycluron Chemical compound CN(C)C(=O)NC1CCCCCCC1 DQZCVNGCTZLGAQ-UHFFFAOYSA-N 0.000 claims 1
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 claims 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 claims 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims 1
- 102000002322 Egg Proteins Human genes 0.000 claims 1
- 108010000912 Egg Proteins Proteins 0.000 claims 1
- 101000687448 Homo sapiens REST corepressor 1 Proteins 0.000 claims 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 1
- 150000008575 L-amino acids Chemical class 0.000 claims 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims 1
- 125000003047 N-acetyl group Chemical group 0.000 claims 1
- IUPXFQZBIVXVGN-UHFFFAOYSA-N NC(N1CCCCC1)=[S+]CC1=CC=CC=C1 Chemical compound NC(N1CCCCC1)=[S+]CC1=CC=CC=C1 IUPXFQZBIVXVGN-UHFFFAOYSA-N 0.000 claims 1
- 102100024864 REST corepressor 1 Human genes 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims 1
- 229960003767 alanine Drugs 0.000 claims 1
- 235000004279 alanine Nutrition 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 238000007098 aminolysis reaction Methods 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 238000005815 base catalysis Methods 0.000 claims 1
- JPYQFYIEOUVJDU-UHFFFAOYSA-N beclamide Chemical compound ClCCC(=O)NCC1=CC=CC=C1 JPYQFYIEOUVJDU-UHFFFAOYSA-N 0.000 claims 1
- NJAPCAIWQRPQPY-UHFFFAOYSA-N benzyl hydrogen carbonate Chemical class OC(=O)OCC1=CC=CC=C1 NJAPCAIWQRPQPY-UHFFFAOYSA-N 0.000 claims 1
- LUFPJJNWMYZRQE-UHFFFAOYSA-N benzylsulfanylmethylbenzene Chemical compound C=1C=CC=CC=1CSCC1=CC=CC=C1 LUFPJJNWMYZRQE-UHFFFAOYSA-N 0.000 claims 1
- AWHNUHMUCGRKRA-UHFFFAOYSA-N benzylsulfonylmethylbenzene Chemical compound C=1C=CC=CC=1CS(=O)(=O)CC1=CC=CC=C1 AWHNUHMUCGRKRA-UHFFFAOYSA-N 0.000 claims 1
- 229960003369 butacaine Drugs 0.000 claims 1
- 150000001718 carbodiimides Chemical class 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 101150052795 cbh-1 gene Proteins 0.000 claims 1
- 230000008859 change Effects 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 150000001805 chlorine compounds Chemical class 0.000 claims 1
- 235000012000 cholesterol Nutrition 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- 238000007796 conventional method Methods 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 claims 1
- FQQOMPOPYZIROF-UHFFFAOYSA-N cyclopenta-2,4-dien-1-one Chemical compound O=C1C=CC=C1 FQQOMPOPYZIROF-UHFFFAOYSA-N 0.000 claims 1
- JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 claims 1
- 150000001983 dialkylethers Chemical class 0.000 claims 1
- 230000008034 disappearance Effects 0.000 claims 1
- 235000013345 egg yolk Nutrition 0.000 claims 1
- 210000002969 egg yolk Anatomy 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- QIGLJVBIRIXQRN-ZETCQYMHSA-N ethyl (2s)-2-amino-4-methylpentanoate Chemical compound CCOC(=O)[C@@H](N)CC(C)C QIGLJVBIRIXQRN-ZETCQYMHSA-N 0.000 claims 1
- XSXLCQLOFRENHC-UHFFFAOYSA-N ethyl n-benzylcarbamate Chemical compound CCOC(=O)NCC1=CC=CC=C1 XSXLCQLOFRENHC-UHFFFAOYSA-N 0.000 claims 1
- LBKPGNUOUPTQKA-UHFFFAOYSA-N ethyl n-phenylcarbamate Chemical compound CCOC(=O)NC1=CC=CC=C1 LBKPGNUOUPTQKA-UHFFFAOYSA-N 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- 238000002474 experimental method Methods 0.000 claims 1
- 239000000284 extract Substances 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 239000012065 filter cake Substances 0.000 claims 1
- RZILCCPWPBTYDO-UHFFFAOYSA-N fluometuron Chemical compound CN(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 RZILCCPWPBTYDO-UHFFFAOYSA-N 0.000 claims 1
- 235000003599 food sweetener Nutrition 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000005457 ice water Substances 0.000 claims 1
- 239000011261 inert gas Substances 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 239000000155 melt Substances 0.000 claims 1
- MVOSXBFYMONFPD-VIFPVBQESA-N methyl (2s)-2-(benzylcarbamoylamino)propanoate Chemical compound COC(=O)[C@H](C)NC(=O)NCC1=CC=CC=C1 MVOSXBFYMONFPD-VIFPVBQESA-N 0.000 claims 1
- VSDUZFOSJDMAFZ-VIFPVBQESA-N methyl L-phenylalaninate Chemical compound COC(=O)[C@@H](N)CC1=CC=CC=C1 VSDUZFOSJDMAFZ-VIFPVBQESA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 claims 1
- 239000012452 mother liquor Substances 0.000 claims 1
- 238000003541 multi-stage reaction Methods 0.000 claims 1
- HYRDTOIPWXXZCJ-UHFFFAOYSA-N n-benzyl-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NCC1=CC=CC=C1 HYRDTOIPWXXZCJ-UHFFFAOYSA-N 0.000 claims 1
- UZJLYRRDVFWSGA-UHFFFAOYSA-N n-benzylacetamide Chemical compound CC(=O)NCC1=CC=CC=C1 UZJLYRRDVFWSGA-UHFFFAOYSA-N 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- WTINXWQZWVOQBO-UHFFFAOYSA-N o-(benzenecarbonothioyl) benzenecarbothioate Chemical compound C=1C=CC=CC=1C(=S)OC(=S)C1=CC=CC=C1 WTINXWQZWVOQBO-UHFFFAOYSA-N 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 150000003901 oxalic acid esters Chemical class 0.000 claims 1
- 125000003431 oxalo group Chemical group 0.000 claims 1
- 229910052760 oxygen Chemical group 0.000 claims 1
- 230000020477 pH reduction Effects 0.000 claims 1
- 238000005897 peptide coupling reaction Methods 0.000 claims 1
- 238000010647 peptide synthesis reaction Methods 0.000 claims 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims 1
- 238000012545 processing Methods 0.000 claims 1
- 230000002035 prolonged effect Effects 0.000 claims 1
- 150000003151 propanoic acid esters Chemical class 0.000 claims 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 claims 1
- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 230000006340 racemization Effects 0.000 claims 1
- 239000012048 reactive intermediate Substances 0.000 claims 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 claims 1
- 238000004611 spectroscopical analysis Methods 0.000 claims 1
- 238000003860 storage Methods 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 239000003765 sweetening agent Substances 0.000 claims 1
- RJBVJBGFJIHJSZ-ZETCQYMHSA-N tert-butyl (2s)-2-amino-3-methylbutanoate Chemical compound CC(C)[C@H](N)C(=O)OC(C)(C)C RJBVJBGFJIHJSZ-ZETCQYMHSA-N 0.000 claims 1
- 150000007970 thio esters Chemical class 0.000 claims 1
- 150000003564 thiocarbonyl compounds Chemical class 0.000 claims 1
- 229960004295 valine Drugs 0.000 claims 1
- 239000004474 valine Substances 0.000 claims 1
- 125000000468 ketone group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1809—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/46—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings substituted on the ring sulfur atom
- C07D333/48—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings substituted on the ring sulfur atom by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J33/00—Normal steroids having a sulfur-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J33/002—Normal steroids having a sulfur-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0055—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06078—Dipeptides with the first amino acid being neutral and aromatic or cycloaliphatic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
- C07K5/06165—Dipeptides with the first amino acid being heterocyclic and Pro-amino acid; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0821—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp
- C07K5/0823—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp and Pro-amino acid; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
- C07K5/1024—Tetrapeptides with the first amino acid being heterocyclic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2625539A DE2625539C2 (de) | 1976-06-05 | 1976-06-05 | Cyclische Ester des 3,4-Dihydroxy-2,5-diphenyl-thiophen-1,1-dioxids und des 3,4-Dihydroxy-2,5-diphenyl-cyclopentadienons und deren Verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1578963A true GB1578963A (en) | 1980-11-12 |
Family
ID=5980017
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB23381/77A Expired GB1578963A (en) | 1976-06-05 | 1977-06-02 | Cyclic esters of 3,4-dihydroxy-thiophene-1,1-dioxide compounds and 3,4-dihydroxy-cyclopentadienone compounds and their use as intermediates |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4122090A (https=) |
| CA (1) | CA1106388A (https=) |
| CH (1) | CH636877A5 (https=) |
| DE (1) | DE2625539C2 (https=) |
| FR (1) | FR2353555A1 (https=) |
| GB (1) | GB1578963A (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022238174A1 (en) * | 2021-05-10 | 2022-11-17 | Dsm Ip Assets B.V. | Purification of specific tripeptide by use of ethers |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1186733B (it) * | 1985-06-05 | 1987-12-16 | Eniricerche Spa | Composti tripeptidici ad azione ipotensiva |
| CN1122656C (zh) * | 2000-06-26 | 2003-10-01 | 席振峰 | 带有碳1到碳12的烷基或芳香基取代基的环戊二烯酮衍生物的合成方法 |
| ITRM20060090A1 (it) * | 2006-02-22 | 2007-08-23 | Sigma Tau Ind Farmaceuti | Nuovi composti inibitori cpt a livello del snc come farmaci antidiabetici e o antiobesita |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3306912A (en) * | 1964-09-14 | 1967-02-28 | Union Carbide Corp | Sulfolanyl polyamines and method for their production |
| US3706769A (en) * | 1970-06-08 | 1972-12-19 | Ciba Geigy Corp | Thiophene-1,1-dioxides |
-
1976
- 1976-06-05 DE DE2625539A patent/DE2625539C2/de not_active Expired
-
1977
- 1977-05-30 CA CA279,418A patent/CA1106388A/en not_active Expired
- 1977-05-31 US US05/801,560 patent/US4122090A/en not_active Expired - Lifetime
- 1977-06-02 GB GB23381/77A patent/GB1578963A/en not_active Expired
- 1977-06-02 CH CH680177A patent/CH636877A5/de not_active IP Right Cessation
- 1977-06-03 FR FR7716987A patent/FR2353555A1/fr active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022238174A1 (en) * | 2021-05-10 | 2022-11-17 | Dsm Ip Assets B.V. | Purification of specific tripeptide by use of ethers |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2353555B1 (https=) | 1982-12-31 |
| DE2625539C2 (de) | 1982-11-04 |
| CA1106388A (en) | 1981-08-04 |
| US4122090A (en) | 1978-10-24 |
| FR2353555A1 (fr) | 1977-12-30 |
| DE2625539A1 (de) | 1977-12-22 |
| CH636877A5 (de) | 1983-06-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19930602 |