CH624664A5 - Process for preparing novel carbonic esters - Google Patents
Process for preparing novel carbonic esters Download PDFInfo
- Publication number
- CH624664A5 CH624664A5 CH1111175A CH1111175A CH624664A5 CH 624664 A5 CH624664 A5 CH 624664A5 CH 1111175 A CH1111175 A CH 1111175A CH 1111175 A CH1111175 A CH 1111175A CH 624664 A5 CH624664 A5 CH 624664A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- lower alkyl
- cyano
- group
- aryl
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000002148 esters Chemical class 0.000 title 1
- -1 formic acid ester Chemical class 0.000 claims description 57
- 150000001875 compounds Chemical class 0.000 claims description 51
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 150000002367 halogens Chemical class 0.000 claims description 24
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
- 150000004651 carbonic acid esters Chemical class 0.000 claims description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 11
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 11
- 125000003435 aroyl group Chemical group 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 125000001589 carboacyl group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 150000002440 hydroxy compounds Chemical class 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 2
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 174
- 239000000243 solution Substances 0.000 description 132
- 239000000203 mixture Substances 0.000 description 110
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 78
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 73
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 71
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 57
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 56
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 38
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 37
- 239000011541 reaction mixture Substances 0.000 description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 28
- 239000013078 crystal Substances 0.000 description 28
- 239000002904 solvent Substances 0.000 description 26
- 238000001816 cooling Methods 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 19
- 235000019341 magnesium sulphate Nutrition 0.000 description 19
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 18
- 235000017557 sodium bicarbonate Nutrition 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 17
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
- 238000001914 filtration Methods 0.000 description 16
- 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 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000010410 layer Substances 0.000 description 15
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 14
- 239000003921 oil Substances 0.000 description 14
- 239000011780 sodium chloride Substances 0.000 description 13
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 12
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000000862 absorption spectrum Methods 0.000 description 12
- 239000007858 starting material Substances 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 11
- 239000003208 petroleum Substances 0.000 description 11
- QQWYQAQQADNEIC-UHFFFAOYSA-N tert-butyl [[cyano(phenyl)methylidene]amino] carbonate Chemical compound CC(C)(C)OC(=O)ON=C(C#N)C1=CC=CC=C1 QQWYQAQQADNEIC-UHFFFAOYSA-N 0.000 description 11
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 239000002198 insoluble material Substances 0.000 description 9
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- MJCQFBKIFDVTTR-NTMALXAHSA-N (hydroxyimino)(phenyl)acetonitrile Chemical compound O\N=C(\C#N)C1=CC=CC=C1 MJCQFBKIFDVTTR-NTMALXAHSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 8
- WYRIRZDRBQZVRA-UHFFFAOYSA-N diethyl 2-[(2-methylpropan-2-yl)oxycarbonyloxyimino]propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)=NOC(=O)OC(C)(C)C WYRIRZDRBQZVRA-UHFFFAOYSA-N 0.000 description 7
- 239000000539 dimer Substances 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- MSHFRERJPWKJFX-UHFFFAOYSA-N 4-Methoxybenzyl alcohol Chemical compound COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- 239000004471 Glycine Substances 0.000 description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 6
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 6
- 229960005190 phenylalanine Drugs 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- KUHUCVAPDMOVSL-UHFFFAOYSA-N (benzhydrylideneamino) tert-butyl carbonate Chemical compound C=1C=CC=CC=1C(=NOC(=O)OC(C)(C)C)C1=CC=CC=C1 KUHUCVAPDMOVSL-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- APDCWEJPUJDKNC-UHFFFAOYSA-N [[cyano(phenyl)methylidene]amino] carbonochloridate Chemical compound ClC(=O)ON=C(C#N)C1=CC=CC=C1 APDCWEJPUJDKNC-UHFFFAOYSA-N 0.000 description 4
- UARDXIXWKAZPPS-UHFFFAOYSA-N benzotriazol-1-yl benzyl carbonate Chemical compound N1=NC2=CC=CC=C2N1OC(=O)OCC1=CC=CC=C1 UARDXIXWKAZPPS-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- ZWAUCKIVUDUMAU-UHFFFAOYSA-N diethyl 2-[(4-methoxyphenyl)methoxycarbonyloxyimino]propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)=NOC(=O)OCC1=CC=C(OC)C=C1 ZWAUCKIVUDUMAU-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000012452 mother liquor Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- ZUVNAZNPUDSONZ-UHFFFAOYSA-N tert-butyl [(1,3-dioxo-1-phenylbutan-2-ylidene)amino] carbonate Chemical compound CC(C)(C)OC(=O)ON=C(C(=O)C)C(=O)C1=CC=CC=C1 ZUVNAZNPUDSONZ-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 101150041968 CDC13 gene Proteins 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- VTSKHZORADYRJT-UHFFFAOYSA-N [[cyano(phenyl)methylidene]amino] 2,2,2-trichloroethyl carbonate Chemical compound ClC(Cl)(Cl)COC(=O)ON=C(C#N)C1=CC=CC=C1 VTSKHZORADYRJT-UHFFFAOYSA-N 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 3
- 150000008041 alkali metal carbonates Chemical class 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 3
- 239000000920 calcium hydroxide Substances 0.000 description 3
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- WAUNZNLUNHZURY-UHFFFAOYSA-N ethyl 2-[(2-methylpropan-2-yl)oxycarbonyloxyimino]-3-oxobutanoate Chemical compound CCOC(=O)C(C(C)=O)=NOC(=O)OC(C)(C)C WAUNZNLUNHZURY-UHFFFAOYSA-N 0.000 description 3
- RTQZMFXONIYPJH-UHFFFAOYSA-N ethyl 2-cyano-2-phenylmethoxycarbonyloxyiminoacetate Chemical compound CCOC(=O)C(C#N)=NOC(=O)OCC1=CC=CC=C1 RTQZMFXONIYPJH-UHFFFAOYSA-N 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 3
- 239000001095 magnesium carbonate Substances 0.000 description 3
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 3
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 3
- 239000000347 magnesium hydroxide Substances 0.000 description 3
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 3
- 235000015497 potassium bicarbonate Nutrition 0.000 description 3
- 239000011736 potassium bicarbonate Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- DCXVVFFQOQDJTO-UHFFFAOYSA-N tert-butyl [[(4-chlorophenyl)-cyanomethylidene]amino] carbonate Chemical compound CC(C)(C)OC(=O)ON=C(C#N)C1=CC=C(Cl)C=C1 DCXVVFFQOQDJTO-UHFFFAOYSA-N 0.000 description 3
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 3
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- UVWJYTBVDBCVGT-INIZCTEOSA-N (2s)-2-[(4-methoxyphenyl)methoxycarbonylamino]-3-phenylpropanoic acid Chemical compound C1=CC(OC)=CC=C1COC(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 UVWJYTBVDBCVGT-INIZCTEOSA-N 0.000 description 2
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- HMIPGQAPRXZOFS-UHFFFAOYSA-N (6-chlorobenzotriazol-1-yl) ethyl carbonate Chemical compound C1=C(Cl)C=C2N(OC(=O)OCC)N=NC2=C1 HMIPGQAPRXZOFS-UHFFFAOYSA-N 0.000 description 2
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- MRAUNPAHJZDYCK-BYPYZUCNSA-N L-nitroarginine Chemical compound OC(=O)[C@@H](N)CCCNC(=N)N[N+]([O-])=O MRAUNPAHJZDYCK-BYPYZUCNSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- RBLQMAMPPCPBKT-UHFFFAOYSA-N [(2-amino-1-cyano-2-oxoethylidene)amino] 2-methylpropyl carbonate Chemical compound CC(C)COC(=O)ON=C(C#N)C(N)=O RBLQMAMPPCPBKT-UHFFFAOYSA-N 0.000 description 2
- ZTQALNAJBSYVGD-UHFFFAOYSA-N [(2-amino-1-cyano-2-oxoethylidene)amino] ethyl carbonate Chemical compound CCOC(=O)ON=C(C#N)C(N)=O ZTQALNAJBSYVGD-UHFFFAOYSA-N 0.000 description 2
- QTJLINZGLKRYPV-UHFFFAOYSA-N [(2-amino-1-cyano-2-oxoethylidene)amino] methyl carbonate Chemical compound COC(=O)ON=C(C#N)C(N)=O QTJLINZGLKRYPV-UHFFFAOYSA-N 0.000 description 2
- IPRBOQUKBZNCAG-MNDPQUGUSA-N [(e)-[cyano(phenyl)methylidene]amino] (4-methoxyphenyl)methyl carbonate Chemical compound C1=CC(OC)=CC=C1COC(=O)O\N=C(\C#N)C1=CC=CC=C1 IPRBOQUKBZNCAG-MNDPQUGUSA-N 0.000 description 2
- IPRBOQUKBZNCAG-UHFFFAOYSA-N [[cyano(phenyl)methylidene]amino] (4-methoxyphenyl)methyl carbonate Chemical compound C1=CC(OC)=CC=C1COC(=O)ON=C(C#N)C1=CC=CC=C1 IPRBOQUKBZNCAG-UHFFFAOYSA-N 0.000 description 2
- UEGOPGSETFMNJW-UHFFFAOYSA-N [[cyano(phenyl)methylidene]amino] 1-cyclopropylethyl carbonate Chemical compound C1CC1C(C)OC(=O)ON=C(C#N)C1=CC=CC=C1 UEGOPGSETFMNJW-UHFFFAOYSA-N 0.000 description 2
- 229960003767 alanine Drugs 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- KOZNRINGOBVQEO-UHFFFAOYSA-N benzyl [[cyano(phenyl)methylidene]amino] carbonate Chemical compound C=1C=CC=CC=1C(C#N)=NOC(=O)OCC1=CC=CC=C1 KOZNRINGOBVQEO-UHFFFAOYSA-N 0.000 description 2
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
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- WSRJXACIYSJQLP-UHFFFAOYSA-N ethyl 2-cyano-2-ethoxycarbonyloxyiminoacetate Chemical compound CCOC(=O)ON=C(C#N)C(=O)OCC WSRJXACIYSJQLP-UHFFFAOYSA-N 0.000 description 2
- YVLYRIWISYQNKJ-UHFFFAOYSA-N ethyl 2-cyano-2-methoxycarbonyloxyiminoacetate Chemical compound CCOC(=O)C(C#N)=NOC(=O)OC YVLYRIWISYQNKJ-UHFFFAOYSA-N 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
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- 125000005843 halogen group Chemical group 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
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- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
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- FBDOCAALFYQQPE-UHFFFAOYSA-N tert-butyl [[cyano(naphthalen-1-yl)methylidene]amino] carbonate Chemical compound C1=CC=C2C(C(C#N)=NOC(=O)OC(C)(C)C)=CC=CC2=C1 FBDOCAALFYQQPE-UHFFFAOYSA-N 0.000 description 2
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- UWAGMHGGFXIUHH-SECBINFHSA-N (2R)-2-amino-2-[3-[bis(methylsulfonyl)amino]phenyl]acetic acid Chemical compound CS(=O)(=O)N(S(C)(=O)=O)C1=CC=CC([C@@H](N)C(O)=O)=C1 UWAGMHGGFXIUHH-SECBINFHSA-N 0.000 description 1
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- AQHXLTAYMNQGLT-UHFFFAOYSA-N (benzhydrylideneamino) carbonochloridate Chemical compound C=1C=CC=CC=1C(=NOC(=O)Cl)C1=CC=CC=C1 AQHXLTAYMNQGLT-UHFFFAOYSA-N 0.000 description 1
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- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
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- 101000605127 Homo sapiens Prostaglandin G/H synthase 2 Proteins 0.000 description 1
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- XBFNRAXPBCDSNR-UHFFFAOYSA-N [(1,3-dioxo-1-phenylbutan-2-ylidene)amino] carbonochloridate Chemical compound ClC(=O)ON=C(C(=O)C)C(=O)C1=CC=CC=C1 XBFNRAXPBCDSNR-UHFFFAOYSA-N 0.000 description 1
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- 150000001491 aromatic compounds Chemical class 0.000 description 1
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- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
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- 230000005587 bubbling Effects 0.000 description 1
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- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
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- 150000001780 cephalosporins Chemical class 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 125000002592 cumenyl group Chemical group C1(=C(C=CC=C1)*)C(C)C 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
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- ZLLOLSCSIGZQEE-UHFFFAOYSA-N diethyl 2-carbonochloridoyloxyiminopropanedioate Chemical compound CCOC(=O)C(=NOC(Cl)=O)C(=O)OCC ZLLOLSCSIGZQEE-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- RCKRTBLMGGXYIR-UHFFFAOYSA-N ethyl 2-cyano-2-(2,2,2-trichloroethoxycarbonyloxyimino)acetate Chemical compound CCOC(=O)C(C#N)=NOC(=O)OCC(Cl)(Cl)Cl RCKRTBLMGGXYIR-UHFFFAOYSA-N 0.000 description 1
- QJIZDORCVOXUKP-UHFFFAOYSA-N ethyl 2-cyano-2-(2-methylbutan-2-yloxycarbonyloxyimino)acetate Chemical compound CCOC(=O)C(C#N)=NOC(=O)OC(C)(C)CC QJIZDORCVOXUKP-UHFFFAOYSA-N 0.000 description 1
- IACSYDRIOYGJNH-UHFFFAOYSA-N ethyl 2-hydroxyimino-3-oxobutanoate Chemical compound CCOC(=O)C(=NO)C(C)=O IACSYDRIOYGJNH-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
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- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
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- 229960003136 leucine Drugs 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 229960004452 methionine Drugs 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- BLLFVUPNHCTMSV-UHFFFAOYSA-N methyl nitrite Chemical compound CON=O BLLFVUPNHCTMSV-UHFFFAOYSA-N 0.000 description 1
- JDEJGVSZUIJWBM-UHFFFAOYSA-N n,n,2-trimethylaniline Chemical compound CN(C)C1=CC=CC=C1C JDEJGVSZUIJWBM-UHFFFAOYSA-N 0.000 description 1
- DNYZBFWKVMKMRM-UHFFFAOYSA-N n-benzhydrylidenehydroxylamine Chemical compound C=1C=CC=CC=1C(=NO)C1=CC=CC=C1 DNYZBFWKVMKMRM-UHFFFAOYSA-N 0.000 description 1
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
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- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
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- 229960002429 proline Drugs 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- KZUZIRNOOCLTOG-UHFFFAOYSA-N tert-butyl (6-chlorobenzotriazol-1-yl) carbonate Chemical compound C1=C(Cl)C=C2N(OC(=O)OC(C)(C)C)N=NC2=C1 KZUZIRNOOCLTOG-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/06—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9870274A JPS5126801A (ja) | 1974-08-27 | 1974-08-27 | Aminoki no hogohoho |
| JP10936274A JPS5828273B2 (ja) | 1974-09-21 | 1974-09-21 | タンサンエステルルイ ノ ゴウセイホウ |
| JP11585674A JPS5828274B2 (ja) | 1974-10-07 | 1974-10-07 | タンサンエステルルイオセイゾウスル ホウホウ |
| JP1670775A JPS50124504A (OSRAM) | 1975-02-07 | 1975-02-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH624664A5 true CH624664A5 (en) | 1981-08-14 |
Family
ID=34923333
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1111175A CH624664A5 (en) | 1974-08-27 | 1975-08-27 | Process for preparing novel carbonic esters |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE832716A (OSRAM) |
| CH (1) | CH624664A5 (OSRAM) |
| DE (1) | DE2538138A1 (OSRAM) |
| FR (1) | FR2286130A1 (OSRAM) |
| NL (1) | NL7510136A (OSRAM) |
| SE (1) | SE436198B (OSRAM) |
-
1975
- 1975-08-25 BE BE159438A patent/BE832716A/xx not_active IP Right Cessation
- 1975-08-26 SE SE7509492A patent/SE436198B/xx unknown
- 1975-08-27 DE DE19752538138 patent/DE2538138A1/de not_active Withdrawn
- 1975-08-27 CH CH1111175A patent/CH624664A5/de not_active IP Right Cessation
- 1975-08-27 NL NL7510136A patent/NL7510136A/xx not_active Application Discontinuation
- 1975-08-27 FR FR7526422A patent/FR2286130A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| SE7509492L (sv) | 1976-03-01 |
| FR2286130A1 (fr) | 1976-04-23 |
| NL7510136A (nl) | 1976-03-02 |
| DE2538138A1 (de) | 1976-03-11 |
| FR2286130B1 (OSRAM) | 1982-07-09 |
| SE436198B (sv) | 1984-11-19 |
| BE832716A (fr) | 1976-02-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |