JPS59116256A - Ｓ―α―シアノ―３―フェノキシベンジルアルコール類の製造方法 - Google Patents
Ｓ―α―シアノ―３―フェノキシベンジルアルコール類の製造方法Info
- Publication number
- JPS59116256A JPS59116256A JP58220485A JP22048583A JPS59116256A JP S59116256 A JPS59116256 A JP S59116256A JP 58220485 A JP58220485 A JP 58220485A JP 22048583 A JP22048583 A JP 22048583A JP S59116256 A JPS59116256 A JP S59116256A
- Authority
- JP
- Japan
- Prior art keywords
- histidine
- group
- cyclo
- ketene
- item
- 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.)
- Granted
Links
- -1 cyanomethyl ester Chemical class 0.000 title claims description 76
- 238000004519 manufacturing process Methods 0.000 title description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 86
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 82
- 238000000034 method Methods 0.000 claims description 77
- 239000003054 catalyst Substances 0.000 claims description 65
- 239000002253 acid Substances 0.000 claims description 62
- 239000002904 solvent Substances 0.000 claims description 58
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 57
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 claims description 57
- 239000000203 mixture Substances 0.000 claims description 51
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 46
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 43
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims description 43
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 39
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 33
- 239000000047 product Substances 0.000 claims description 33
- 150000004820 halides Chemical class 0.000 claims description 28
- 150000001299 aldehydes Chemical class 0.000 claims description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 239000007795 chemical reaction product Substances 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 235000001014 amino acid Nutrition 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 21
- MRLGCTNJRREZHZ-UHFFFAOYSA-N 3-phenoxybenzaldehyde Chemical class O=CC1=CC=CC(OC=2C=CC=CC=2)=C1 MRLGCTNJRREZHZ-UHFFFAOYSA-N 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 150000002576 ketones Chemical class 0.000 claims description 20
- 150000002148 esters Chemical class 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 150000001413 amino acids Chemical class 0.000 claims description 18
- 229920001184 polypeptide Polymers 0.000 claims description 18
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 150000001412 amines Chemical class 0.000 claims description 15
- 150000003512 tertiary amines Chemical class 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 108010016626 Dipeptides Proteins 0.000 claims description 12
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 10
- 125000001188 haloalkyl group Chemical group 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000000487 histidyl group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C([H])=N1 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 9
- 125000006239 protecting group Chemical group 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 150000004702 methyl esters Chemical class 0.000 claims description 8
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- 150000001408 amides Chemical class 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 125000004185 ester group Chemical group 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- YIWFXZNIBQBFHR-LURJTMIESA-N Gly-His Chemical compound [NH3+]CC(=O)N[C@H](C([O-])=O)CC1=CN=CN1 YIWFXZNIBQBFHR-LURJTMIESA-N 0.000 claims description 6
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 claims description 6
- 108010020688 glycylhistidine Proteins 0.000 claims description 6
- KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical compound OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 claims description 5
- LUTLAXLNPLZCOF-UHFFFAOYSA-N 1-Methylhistidine Natural products OC(=O)C(N)(C)CC1=NC=CN1 LUTLAXLNPLZCOF-UHFFFAOYSA-N 0.000 claims description 5
- BRMWTNUJHUMWMS-UHFFFAOYSA-N 3-Methylhistidine Natural products CN1C=NC(CC(N)C(O)=O)=C1 BRMWTNUJHUMWMS-UHFFFAOYSA-N 0.000 claims description 5
- XZWXFWBHYRFLEF-FSPLSTOPSA-N Ala-His Chemical compound C[C@H](N)C(=O)N[C@H](C(O)=O)CC1=CN=CN1 XZWXFWBHYRFLEF-FSPLSTOPSA-N 0.000 claims description 5
- JDHILDINMRGULE-LURJTMIESA-N N(pros)-methyl-L-histidine Chemical group CN1C=NC=C1C[C@H](N)C(O)=O JDHILDINMRGULE-LURJTMIESA-N 0.000 claims description 5
- BRMWTNUJHUMWMS-LURJTMIESA-N N(tele)-methyl-L-histidine Chemical compound CN1C=NC(C[C@H](N)C(O)=O)=C1 BRMWTNUJHUMWMS-LURJTMIESA-N 0.000 claims description 5
- 108010070944 alanylhistidine Proteins 0.000 claims description 5
- 239000000010 aprotic solvent Substances 0.000 claims description 5
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 108010085443 Anserine Proteins 0.000 claims description 4
- FRJIAZKQGSCKPQ-FSPLSTOPSA-N His-Ala Chemical compound OC(=O)[C@H](C)NC(=O)[C@@H](N)CC1=CN=CN1 FRJIAZKQGSCKPQ-FSPLSTOPSA-N 0.000 claims description 4
- SLRNWACWRVGMKD-UHFFFAOYSA-N L-anserine Natural products CN1C=NC(CC(NC(=O)CCN)C(O)=O)=C1 SLRNWACWRVGMKD-UHFFFAOYSA-N 0.000 claims description 4
- LVVFYANJKYTPCY-OLZOCXBDSA-N N[C@@H](C1=CC=CC=C1)CC(=O)N[C@@H](CC1=CNC=N1)C(=O)O Chemical compound N[C@@H](C1=CC=CC=C1)CC(=O)N[C@@H](CC1=CNC=N1)C(=O)O LVVFYANJKYTPCY-OLZOCXBDSA-N 0.000 claims description 4
- 241000210053 Potentilla elegans Species 0.000 claims description 4
- MYYIAHXIVFADCU-QMMMGPOBSA-N anserine Chemical compound CN1C=NC=C1C[C@H](NC(=O)CC[NH3+])C([O-])=O MYYIAHXIVFADCU-QMMMGPOBSA-N 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 108010040030 histidinoalanine Proteins 0.000 claims description 4
- 238000012546 transfer Methods 0.000 claims description 4
- XRGGOHBVSVCEDQ-KBPBESRZSA-N (2S)-2-[[(2S)-2-amino-3-phenylpropanoyl]-methylamino]-3-(1H-imidazol-5-yl)propanoic acid Chemical compound C([C@H](N(C)C(=O)[C@@H](N)CC=1C=CC=CC=1)C(O)=O)C1=CNC=N1 XRGGOHBVSVCEDQ-KBPBESRZSA-N 0.000 claims description 3
- ZTVUZCVPVXCVRV-KBPBESRZSA-N (2S)-2-[[(2S)-2-amino-4-phenylbutanoyl]amino]-3-(1H-imidazol-5-yl)propanoic acid Chemical compound N[C@@H](CCC1=CC=CC=C1)C(=O)N[C@@H](CC1=CNC=N1)C(=O)O ZTVUZCVPVXCVRV-KBPBESRZSA-N 0.000 claims description 3
- NMXSWQMJOZUQKY-LBPRGKRZSA-N (2s)-2-amino-3-(1-benzylimidazol-4-yl)propanoic acid Chemical compound C1=NC(C[C@H](N)C(O)=O)=CN1CC1=CC=CC=C1 NMXSWQMJOZUQKY-LBPRGKRZSA-N 0.000 claims description 3
- ROSMBSOKFVZTHV-QMMMGPOBSA-N (2s)-2-amino-3-(1-propylimidazol-4-yl)propanoic acid Chemical compound CCCN1C=NC(C[C@H](N)C(O)=O)=C1 ROSMBSOKFVZTHV-QMMMGPOBSA-N 0.000 claims description 3
- SGCGMORCWLEJNZ-UWVGGRQHSA-N His-His Chemical compound C([C@H]([NH3+])C(=O)N[C@@H](CC=1NC=NC=1)C([O-])=O)C1=CN=CN1 SGCGMORCWLEJNZ-UWVGGRQHSA-N 0.000 claims description 3
- LNCFUHAPNTYMJB-IUCAKERBSA-N His-Pro Chemical compound C([C@H](N)C(=O)N1[C@@H](CCC1)C(O)=O)C1=CN=CN1 LNCFUHAPNTYMJB-IUCAKERBSA-N 0.000 claims description 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 3
- 125000003295 alanine group Chemical group N[C@@H](C)C(=O)* 0.000 claims description 3
- HRRYYCWYCMJNGA-ZETCQYMHSA-N alpha-methyl-L-histidine Chemical compound OC(=O)[C@](N)(C)CC1=CN=CN1 HRRYYCWYCMJNGA-ZETCQYMHSA-N 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 3
- XAWDMXNJDWMHCN-KLXURFKVSA-N ethyl (2s)-2-amino-3-(1h-imidazol-5-yl)propanoate;dihydrochloride Chemical compound Cl.Cl.CCOC(=O)[C@@H](N)CC1=CN=CN1 XAWDMXNJDWMHCN-KLXURFKVSA-N 0.000 claims description 3
- 108010028295 histidylhistidine Proteins 0.000 claims description 3
- 108010092114 histidylphenylalanine Proteins 0.000 claims description 3
- 108010085325 histidylproline Proteins 0.000 claims description 3
- 239000012433 hydrogen halide Substances 0.000 claims description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 3
- XWOBNBRUDDUEEY-UHFFFAOYSA-N leucyl-histidine Chemical compound CC(C)CC(N)C(=O)NC(C(O)=O)CC1=CN=CN1 XWOBNBRUDDUEEY-UHFFFAOYSA-N 0.000 claims description 3
- VEEIFXWJNCAVEQ-RGMNGODLSA-N methyl (2s)-2-amino-3-(1h-imidazol-5-yl)propanoate;hydrochloride Chemical compound Cl.COC(=O)[C@@H](N)CC1=CNC=N1 VEEIFXWJNCAVEQ-RGMNGODLSA-N 0.000 claims description 3
- CKFBFQHBUCDOHL-UHFFFAOYSA-N phenoxy(phenyl)methanol Chemical compound C=1C=CC=CC=1C(O)OC1=CC=CC=C1 CKFBFQHBUCDOHL-UHFFFAOYSA-N 0.000 claims description 3
- 239000012970 tertiary amine catalyst Substances 0.000 claims description 3
- AULROAPTZJZHBY-KGLIPLIRSA-N (2S)-2-[[(3R)-3-amino-3-phenylpropanoyl]amino]-3-(1-methylimidazol-4-yl)propanoic acid Chemical compound N[C@@H](C1=CC=CC=C1)CC(=O)N[C@@H](CC1=CN(C=N1)C)C(=O)O AULROAPTZJZHBY-KGLIPLIRSA-N 0.000 claims description 2
- KQLFYKBWIXSKHJ-KGLIPLIRSA-N (2S)-2-[[(3R)-3-amino-3-phenylpropanoyl]amino]-3-(3-methylimidazol-4-yl)propanoic acid Chemical compound N[C@@H](C1=CC=CC=C1)CC(=O)N[C@@H](CC1=CN=CN1C)C(=O)O KQLFYKBWIXSKHJ-KGLIPLIRSA-N 0.000 claims description 2
- XEXSSIBQYNKFBX-KBPBESRZSA-N Phe-Gly-His Chemical compound C([C@H](N)C(=O)NCC(=O)N[C@@H](CC=1N=CNC=1)C(O)=O)C1=CC=CC=C1 XEXSSIBQYNKFBX-KBPBESRZSA-N 0.000 claims description 2
- OHUXOEXBXPZKPT-STQMWFEESA-N Phe-His Chemical compound C([C@H](N)C(=O)N[C@@H](CC=1N=CNC=1)C(O)=O)C1=CC=CC=C1 OHUXOEXBXPZKPT-STQMWFEESA-N 0.000 claims description 2
- FPMLCYUEXWDCDX-WFASDCNBSA-N methyl (2s)-3-(1h-imidazol-5-yl)-2-[[(2s)-2-(phenylmethoxycarbonylamino)propanoyl]amino]propanoate Chemical compound C([C@@H](C(=O)OC)NC(=O)[C@H](C)NC(=O)OCC=1C=CC=CC=1)C1=CNC=N1 FPMLCYUEXWDCDX-WFASDCNBSA-N 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 240000002390 Pandanus odoratissimus Species 0.000 claims 1
- 235000005311 Pandanus odoratissimus Nutrition 0.000 claims 1
- BNQVUHQWZGTIBX-IUCAKERBSA-N Val-His Chemical compound CC(C)[C@H]([NH3+])C(=O)N[C@H](C([O-])=O)CC1=CN=CN1 BNQVUHQWZGTIBX-IUCAKERBSA-N 0.000 claims 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 45
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 31
- 239000000243 solution Substances 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 239000007787 solid Substances 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 125000003118 aryl group Chemical group 0.000 description 18
- 235000019441 ethanol Nutrition 0.000 description 16
- 125000001424 substituent group Chemical group 0.000 description 16
- 125000000753 cycloalkyl group Chemical group 0.000 description 14
- 229910052799 carbon Inorganic materials 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- 150000007513 acids Chemical class 0.000 description 10
- 150000001721 carbon Chemical group 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 10
- 150000002561 ketenes Chemical class 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- LSZVSCXZSRXVOA-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-methylbut-1-en-1-one Chemical group CC(C)C(=C=O)C1=CC=C(Cl)C=C1 LSZVSCXZSRXVOA-UHFFFAOYSA-N 0.000 description 8
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 125000000623 heterocyclic group Chemical group 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 150000001335 aliphatic alkanes Chemical class 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 150000002170 ethers Chemical class 0.000 description 7
- 125000001183 hydrocarbyl group Chemical group 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- OHUXOEXBXPZKPT-CHWSQXEVSA-N (2r)-2-[[(2r)-2-amino-3-phenylpropanoyl]amino]-3-(1h-imidazol-5-yl)propanoic acid Chemical compound C([C@@H](N)C(=O)N[C@H](CC=1NC=NC=1)C(O)=O)C1=CC=CC=C1 OHUXOEXBXPZKPT-CHWSQXEVSA-N 0.000 description 6
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 125000004414 alkyl thio group Chemical group 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 125000002837 carbocyclic group Chemical group 0.000 description 6
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Aalpha Natural products C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 6
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 6
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 6
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 5
- 235000004279 alanine Nutrition 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 5
- 238000007796 conventional method Methods 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- BWPYAVCZZUTOBY-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-methylbutanoyl chloride Chemical compound CC(C)C(C(Cl)=O)C1=CC=C(Cl)C=C1 BWPYAVCZZUTOBY-UHFFFAOYSA-N 0.000 description 4
- GXUQMKBQDGPMKZ-UHFFFAOYSA-N 2-hydroxy-2-(3-phenoxyphenyl)acetonitrile Chemical compound N#CC(O)C1=CC=CC(OC=2C=CC=CC=2)=C1 GXUQMKBQDGPMKZ-UHFFFAOYSA-N 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical class OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 125000002015 acyclic group Chemical group 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 4
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 150000007524 organic acids Chemical group 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
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- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- CHQVQXZFZHACQQ-UHFFFAOYSA-M benzyl(triethyl)azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)CC1=CC=CC=C1 CHQVQXZFZHACQQ-UHFFFAOYSA-M 0.000 description 1
- 125000001743 benzylic group Chemical group 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 125000001314 canonical amino-acid group Chemical group 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- CETPKPWXTFTXFW-UHFFFAOYSA-N carbonyl dichloride;2-(2,2-dibromoethenyl)-1,1-dimethylcyclopropane Chemical compound ClC(Cl)=O.CC1(C)CC1C=C(Br)Br CETPKPWXTFTXFW-UHFFFAOYSA-N 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- MXOAEAUPQDYUQM-UHFFFAOYSA-N chlorphenesin Chemical group OCC(O)COC1=CC=C(Cl)C=C1 MXOAEAUPQDYUQM-UHFFFAOYSA-N 0.000 description 1
- KMPWYEUPVWOPIM-LSOMNZGLSA-N cinchonine Chemical compound C1=CC=C2C([C@@H]([C@H]3N4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-LSOMNZGLSA-N 0.000 description 1
- MDIQXIJPQWLFSD-NJGYIYPDSA-N cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(O)=O MDIQXIJPQWLFSD-NJGYIYPDSA-N 0.000 description 1
- 235000013477 citrulline Nutrition 0.000 description 1
- 229960002173 citrulline Drugs 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- ZWJPCOALBPMBIC-UHFFFAOYSA-N diphenylketene Chemical compound C=1C=CC=CC=1C(=C=O)C1=CC=CC=C1 ZWJPCOALBPMBIC-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 229960002179 ephedrine Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000004969 haloethyl group Chemical group 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 150000002410 histidine derivatives Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000006289 hydroxybenzyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- WZNJWVWKTVETCG-UHFFFAOYSA-N kojic acid Natural products OC(=O)C(N)CN1C=CC(=O)C(O)=C1 WZNJWVWKTVETCG-UHFFFAOYSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229960004502 levodopa Drugs 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- VEEIFXWJNCAVEQ-FYZOBXCZSA-N methyl (2r)-2-amino-3-(1h-imidazol-5-yl)propanoate;hydrochloride Chemical compound Cl.COC(=O)[C@H](N)CC1=CNC=N1 VEEIFXWJNCAVEQ-FYZOBXCZSA-N 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- 229950002289 mimosine Drugs 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 150000002825 nitriles Chemical group 0.000 description 1
- 235000017524 noni Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229960003104 ornithine Drugs 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000005501 phase interface Effects 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 235000008729 phenylalanine Nutrition 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- BIMIJXSZMVGEJR-UHFFFAOYSA-M tetra(nonyl)azanium;hydroxide Chemical compound [OH-].CCCCCCCCC[N+](CCCCCCCCC)(CCCCCCCCC)CCCCCCCCC BIMIJXSZMVGEJR-UHFFFAOYSA-M 0.000 description 1
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- RYVBINGWVJJDPU-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC RYVBINGWVJJDPU-UHFFFAOYSA-M 0.000 description 1
- UJMLRSWRUXXZEW-UHFFFAOYSA-M tributyl(octyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCC[P+](CCCC)(CCCC)CCCC UJMLRSWRUXXZEW-UHFFFAOYSA-M 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- SZYJELPVAFJOGJ-UHFFFAOYSA-N trimethylamine hydrochloride Chemical compound Cl.CN(C)C SZYJELPVAFJOGJ-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44351382A | 1982-11-22 | 1982-11-22 | |
| US443513 | 1982-11-22 | ||
| US443764 | 1982-11-22 | ||
| US443763 | 1982-11-22 |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1302306A Division JPH02270852A (ja) | 1982-11-22 | 1989-11-22 | 光学活性シアノメチルエステルの製造方法 |
| JP2164329A Division JPH03238053A (ja) | 1982-11-22 | 1990-06-25 | シクロ（ｄ―フエニルアラニル―ｄ―ヒスチジル）ジペプチド触媒 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59116256A true JPS59116256A (ja) | 1984-07-05 |
| JPH0333151B2 JPH0333151B2 (enrdf_load_stackoverflow) | 1991-05-16 |
Family
ID=23761082
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58220485A Granted JPS59116256A (ja) | 1982-11-22 | 1983-11-21 | Ｓ―α―シアノ―３―フェノキシベンジルアルコール類の製造方法 |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS59116256A (enrdf_load_stackoverflow) |
| DD (1) | DD231344A5 (enrdf_load_stackoverflow) |
| GT (1) | GT198304141A (enrdf_load_stackoverflow) |
| ZA (1) | ZA837994B (enrdf_load_stackoverflow) |
| ZM (1) | ZM8083A1 (enrdf_load_stackoverflow) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62255464A (ja) * | 1986-04-28 | 1987-11-07 | Sumitomo Chem Co Ltd | 光学活性シアンヒドリン化合物の製造法 |
| JPH03238053A (ja) * | 1982-11-22 | 1991-10-23 | E I Du Pont De Nemours & Co | シクロ（ｄ―フエニルアラニル―ｄ―ヒスチジル）ジペプチド触媒 |
| US6204406B1 (en) | 1989-09-29 | 2001-03-20 | Sumitomo Chemical Co., Ltd. | Catalyst for asymmetric induction |
| JP2003531197A (ja) * | 2000-04-20 | 2003-10-21 | デグサ アクチエンゲゼルシャフト | ２，５−ジケトピペラジンの製造方法、２，５−ジケトピペラジン、ジペプチド及びその使用 |
| JP2006518729A (ja) * | 2003-02-24 | 2006-08-17 | シンジェンタ リミテッド | ガンマ−シハロトリンの調製方法 |
| JP2023503962A (ja) * | 2019-11-29 | 2023-02-01 | オートバーン セラピューティクス，インク． | 新規な甲状腺ホルモン模倣物 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5829757A (ja) * | 1981-08-17 | 1983-02-22 | Nippon Kayaku Co Ltd | 光学活性マンデロニトリルの製造法 |
-
1983
- 1983-10-27 ZA ZA837994A patent/ZA837994B/xx unknown
- 1983-11-08 ZM ZM80/83A patent/ZM8083A1/xx unknown
- 1983-11-17 DD DD83272653A patent/DD231344A5/de unknown
- 1983-11-21 JP JP58220485A patent/JPS59116256A/ja active Granted
- 1983-11-21 GT GT198304141A patent/GT198304141A/es unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5829757A (ja) * | 1981-08-17 | 1983-02-22 | Nippon Kayaku Co Ltd | 光学活性マンデロニトリルの製造法 |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03238053A (ja) * | 1982-11-22 | 1991-10-23 | E I Du Pont De Nemours & Co | シクロ（ｄ―フエニルアラニル―ｄ―ヒスチジル）ジペプチド触媒 |
| JPS62255464A (ja) * | 1986-04-28 | 1987-11-07 | Sumitomo Chem Co Ltd | 光学活性シアンヒドリン化合物の製造法 |
| US6204406B1 (en) | 1989-09-29 | 2001-03-20 | Sumitomo Chemical Co., Ltd. | Catalyst for asymmetric induction |
| JP2003531197A (ja) * | 2000-04-20 | 2003-10-21 | デグサ アクチエンゲゼルシャフト | ２，５−ジケトピペラジンの製造方法、２，５−ジケトピペラジン、ジペプチド及びその使用 |
| JP2006518729A (ja) * | 2003-02-24 | 2006-08-17 | シンジェンタ リミテッド | ガンマ−シハロトリンの調製方法 |
| JP2023503962A (ja) * | 2019-11-29 | 2023-02-01 | オートバーン セラピューティクス，インク． | 新規な甲状腺ホルモン模倣物 |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA837994B (en) | 1984-06-27 |
| JPH0333151B2 (enrdf_load_stackoverflow) | 1991-05-16 |
| ZM8083A1 (en) | 1984-10-22 |
| GT198304141A (es) | 1985-05-14 |
| DD231344A5 (de) | 1985-12-24 |
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