JPS6365062B2 - - Google Patents
Info
- Publication number
- JPS6365062B2 JPS6365062B2 JP18095581A JP18095581A JPS6365062B2 JP S6365062 B2 JPS6365062 B2 JP S6365062B2 JP 18095581 A JP18095581 A JP 18095581A JP 18095581 A JP18095581 A JP 18095581A JP S6365062 B2 JPS6365062 B2 JP S6365062B2
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- aminomethylcyclohexylcarbonyl
- acid
- trans
- cis
- 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
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 51
- 239000002253 acid Substances 0.000 claims description 23
- 238000006317 isomerization reaction Methods 0.000 claims description 19
- NVBZUCIQNYPGCI-UHFFFAOYSA-N 3-[4-[4-(aminomethyl)cyclohexanecarbonyl]phenyl]propanoic acid Chemical class C1CC(CN)CCC1C(=O)C1=CC=C(CCC(O)=O)C=C1 NVBZUCIQNYPGCI-UHFFFAOYSA-N 0.000 claims description 18
- 239000007864 aqueous solution Substances 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 230000002378 acidificating effect Effects 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- RZMQTFUCPOQJDB-UHFFFAOYSA-N methyl 3-[4-[4-(aminomethyl)cyclohexanecarbonyl]phenyl]propanoate;hydrochloride Chemical compound Cl.C1=CC(CCC(=O)OC)=CC=C1C(=O)C1CCC(CN)CC1 RZMQTFUCPOQJDB-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000013078 crystal Substances 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- SQPDKJPOCJNLSJ-IOJSEOPQSA-N Cl.C1C[C@@H](CN)CC[C@@H]1C(=O)C1=CC=C(CCC(O)=O)C=C1 Chemical compound Cl.C1C[C@@H](CN)CC[C@@H]1C(=O)C1=CC=C(CCC(O)=O)C=C1 SQPDKJPOCJNLSJ-IOJSEOPQSA-N 0.000 description 8
- -1 phenylpropionic acid ester Chemical class 0.000 description 8
- SQPDKJPOCJNLSJ-UHFFFAOYSA-N 3-[4-[4-(aminomethyl)cyclohexanecarbonyl]phenyl]propanoic acid;hydrochloride Chemical compound Cl.C1CC(CN)CCC1C(=O)C1=CC=C(CCC(O)=O)C=C1 SQPDKJPOCJNLSJ-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 6
- GYDJEQRTZSCIOI-UHFFFAOYSA-N Tranexamic acid Chemical compound NCC1CCC(C(O)=O)CC1 GYDJEQRTZSCIOI-UHFFFAOYSA-N 0.000 description 5
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 5
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 4
- 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 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- NVBZUCIQNYPGCI-CTYIDZIISA-N rotraxate Chemical class C1C[C@@H](CN)CC[C@@H]1C(=O)C1=CC=C(CCC(O)=O)C=C1 NVBZUCIQNYPGCI-CTYIDZIISA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000000767 anti-ulcer Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- RPUSRLKKXPQSGP-UHFFFAOYSA-N methyl 3-phenylpropanoate Chemical compound COC(=O)CCC1=CC=CC=C1 RPUSRLKKXPQSGP-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- RZMQTFUCPOQJDB-SWQINVOKSA-N Cl.NC[C@@H]1CC[C@H](CC1)C(=O)C1=CC=C(C=C1)CCC(=O)OC Chemical compound Cl.NC[C@@H]1CC[C@H](CC1)C(=O)C1=CC=C(C=C1)CCC(=O)OC RZMQTFUCPOQJDB-SWQINVOKSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- JBSSXJMHNNLSPM-UHFFFAOYSA-N butyl 3-[4-[4-(aminomethyl)cyclohexanecarbonyl]phenyl]propanoate Chemical compound NCC1CCC(CC1)C(=O)C1=CC=C(C=C1)CCC(=O)OCCCC JBSSXJMHNNLSPM-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- DZIQUZJSNSZOCH-UHFFFAOYSA-N methyl 2-phenylpropanoate Chemical compound COC(=O)C(C)C1=CC=CC=C1 DZIQUZJSNSZOCH-UHFFFAOYSA-N 0.000 description 1
- UHQSIWDREFJPDI-UHFFFAOYSA-N methyl 3-[4-[4-(aminomethyl)cyclohexanecarbonyl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C(=O)C1CCC(CN)CC1 UHQSIWDREFJPDI-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- ZVTCLUKGWYEQHY-UHFFFAOYSA-N propyl 3-[4-[4-(aminomethyl)cyclohexanecarbonyl]phenyl]propanoate Chemical compound NCC1CCC(CC1)C(=O)C1=CC=C(C=C1)CCC(=O)OCCC ZVTCLUKGWYEQHY-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- ROBLTDOHDSGGDT-UHFFFAOYSA-M sodium;pentane-1-sulfonate Chemical compound [Na+].CCCCCS([O-])(=O)=O ROBLTDOHDSGGDT-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 229940066528 trichloroacetate Drugs 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18095581A JPS5883663A (ja) | 1981-11-13 | 1981-11-13 | ３−〔ｐ−（４−アミノメチルシクロヘキシルカルボニル）フエニル〕プロピオン酸類の異性化方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18095581A JPS5883663A (ja) | 1981-11-13 | 1981-11-13 | ３−〔ｐ−（４−アミノメチルシクロヘキシルカルボニル）フエニル〕プロピオン酸類の異性化方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5883663A JPS5883663A (ja) | 1983-05-19 |
| JPS6365062B2 true JPS6365062B2 (zh) | 1988-12-14 |
Family
ID=16092192
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18095581A Granted JPS5883663A (ja) | 1981-11-13 | 1981-11-13 | ３−〔ｐ−（４−アミノメチルシクロヘキシルカルボニル）フエニル〕プロピオン酸類の異性化方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5883663A (zh) |
-
1981
- 1981-11-13 JP JP18095581A patent/JPS5883663A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5883663A (ja) | 1983-05-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4337352A (en) | Separation of enantiomers of chiral carboxylic acids | |
| EP0075318A2 (en) | p-Hydroxyphenylglycine alpha-phenylethanesulfonate, process for production thereof and utilization thereof in resolution of p-hydroxyphenylglycine | |
| KR100224330B1 (ko) | 골관절 질환의 치료에 유용한 n-((4,5-디히드록시-및 4,5,8-트리히드록시-9,10-디히드로-9,10-디옥소-2-안트라센-일)카르보닐)아미노산 | |
| US4520205A (en) | Chemical resolution of (+)-2,3-dihydroindole-2-carboxylic acid | |
| JP4138928B2 (ja) | Ｄ−アロイソロイシンの製造方法および製造の中間体 | |
| JPS6365062B2 (zh) | ||
| JP3719318B2 (ja) | １−エチル−５−ヒドロキシピラゾールの製法 | |
| KR20020091077A (ko) | α-(2-4-디술포페닐)-Ｎ-ｔｅｒｔ-부틸니트론 및 제약상허용되는 그의 염의 신규 제조 방법 | |
| JP3823385B2 (ja) | ２，４，５−トリフルオロ−３−ヨ−ド安息香酸およびそのエステル類の製造方法 | |
| JP3312451B2 (ja) | 光学活性トランス−１，２−ジアミノシクロヘキサン製造法 | |
| JP4397990B2 (ja) | ３−アルキルフラバノノール誘導体の精製法 | |
| JP3628380B2 (ja) | １，４−架橋シクロヘキサン系カルボン酸誘導体の製造方法 | |
| JP2877976B2 (ja) | 光学活性２，４，４−トリメチル−２−シクロヘキセン−１−オール及びその製法 | |
| US6040471A (en) | Method for preparing certain acetonitriles | |
| JPH029028B2 (zh) | ||
| JP2776995B2 (ja) | （Ｒ）−（＋）−ジヒドロ−α−イオノンの製法及びその新規中間体 | |
| JPH01131143A (ja) | ｄ，ｌ−カルニチンニトリルクロライドの光学分割法 | |
| JPS6197250A (ja) | トランス−１，２−ジアミノシクロヘキサンの精製法 | |
| JP2804654B2 (ja) | （Ｓ）−（−）−デヒドロ−α−ダマスコールの製造方法 | |
| JPS61172846A (ja) | （±）−２−クロロプロピオン酸の光学分割法 | |
| JP2917464B2 (ja) | 光学活性１―メチル―３―フェニルプロピルアミンの製法 | |
| JP2003137835A (ja) | （ｒ）−３−ヒドロキシ−３−（２−フェニルエチル）ヘキサン酸の製造方法 | |
| JPS6261584B2 (zh) | ||
| JP2504934B2 (ja) | １，６，７−トリアシルフオルスコリン誘導体 | |
| JP3538889B2 (ja) | アルキルチオアセタミドの製造方法 |