JPH0435464B2 - - Google Patents
Info
- Publication number
- JPH0435464B2 JPH0435464B2 JP57140299A JP14029982A JPH0435464B2 JP H0435464 B2 JPH0435464 B2 JP H0435464B2 JP 57140299 A JP57140299 A JP 57140299A JP 14029982 A JP14029982 A JP 14029982A JP H0435464 B2 JPH0435464 B2 JP H0435464B2
- Authority
- JP
- Japan
- Prior art keywords
- optically active
- dibenzyl
- carboxy
- general formula
- represented
- 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 - Lifetime
Links
- 150000002148 esters Chemical class 0.000 claims description 27
- 239000013078 crystal Substances 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- BSWUHWZVMBPALP-SJORKVTESA-N (4r,5s)-1,3-dibenzyl-5-methoxycarbonyl-2-oxoimidazolidine-4-carboxylic acid Chemical compound N1([C@H]([C@H](N(C1=O)CC=1C=CC=CC=1)C(=O)OC)C(O)=O)CC1=CC=CC=C1 BSWUHWZVMBPALP-SJORKVTESA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 8
- 238000005406 washing Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 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
- 238000000605 extraction Methods 0.000 description 4
- RVNXWRRDPPIXHE-RBUKOAKNSA-N (4s,5r)-1,3-dibenzyl-2-oxo-5-propan-2-yloxycarbonylimidazolidine-4-carboxylic acid Chemical compound N1([C@@H]([C@@H](N(C1=O)CC=1C=CC=CC=1)C(=O)OC(C)C)C(O)=O)CC1=CC=CC=C1 RVNXWRRDPPIXHE-RBUKOAKNSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- RVNXWRRDPPIXHE-MOPGFXCFSA-N (4r,5s)-1,3-dibenzyl-2-oxo-5-propan-2-yloxycarbonylimidazolidine-4-carboxylic acid Chemical compound N1([C@H]([C@H](N(C1=O)CC=1C=CC=CC=1)C(=O)OC(C)C)C(O)=O)CC1=CC=CC=C1 RVNXWRRDPPIXHE-MOPGFXCFSA-N 0.000 description 2
- OUWRJFDZBGBXKT-ZWKOTPCHSA-N (4s,5r)-1,3-dibenzyl-5-ethoxycarbonyl-2-oxoimidazolidine-4-carboxylic acid Chemical compound N1([C@@H]([C@@H](N(C1=O)CC=1C=CC=CC=1)C(=O)OCC)C(O)=O)CC1=CC=CC=C1 OUWRJFDZBGBXKT-ZWKOTPCHSA-N 0.000 description 2
- BSWUHWZVMBPALP-DLBZAZTESA-N (4s,5r)-1,3-dibenzyl-5-methoxycarbonyl-2-oxoimidazolidine-4-carboxylic acid Chemical compound N1([C@@H]([C@@H](N(C1=O)CC=1C=CC=CC=1)C(=O)OC)C(O)=O)CC1=CC=CC=C1 BSWUHWZVMBPALP-DLBZAZTESA-N 0.000 description 2
- -1 (keto-imidazolide)-2-keto-tetrahydrofuran Chemical compound 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- OUWRJFDZBGBXKT-MSOLQXFVSA-N (4r,5s)-1,3-dibenzyl-5-ethoxycarbonyl-2-oxoimidazolidine-4-carboxylic acid Chemical compound N1([C@H]([C@H](N(C1=O)CC=1C=CC=CC=1)C(=O)OCC)C(O)=O)CC1=CC=CC=C1 OUWRJFDZBGBXKT-MSOLQXFVSA-N 0.000 description 1
- DTGGNTMERRTPLR-UHFFFAOYSA-N 1,2-diphenylethanamine Chemical compound C=1C=CC=CC=1C(N)CC1=CC=CC=C1 DTGGNTMERRTPLR-UHFFFAOYSA-N 0.000 description 1
- AZJLZOVPJNPLGE-UHFFFAOYSA-N 1-(4-methylphenyl)-2-phenylethanamine Chemical compound C1=CC(C)=CC=C1C(N)CC1=CC=CC=C1 AZJLZOVPJNPLGE-UHFFFAOYSA-N 0.000 description 1
- DYPUFZGNHHLMAL-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-phenylethanamine Chemical compound C=1C=CC=CC=1C(N)CC1=CC=C(Cl)C=C1 DYPUFZGNHHLMAL-UHFFFAOYSA-N 0.000 description 1
- ZICDZTXDTPZBKH-UHFFFAOYSA-N 2-(4-methylphenyl)-1-phenylethanamine Chemical compound C1=CC(C)=CC=C1CC(N)C1=CC=CC=C1 ZICDZTXDTPZBKH-UHFFFAOYSA-N 0.000 description 1
- OWOUKRYOZIZVFK-UHFFFAOYSA-N 2-methylphenethylamine Chemical compound CC1=CC=CC=C1CCN OWOUKRYOZIZVFK-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000003947 ethylamines Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 150000007925 phenylethylamine derivatives Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- NLYMVJUAPLEDSY-UHFFFAOYSA-N propyl 2-oxoimidazolidine-1-carboxylate Chemical compound CCCOC(=O)N1CCNC1=O NLYMVJUAPLEDSY-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14029982A JPS5929670A (ja) | 1982-08-11 | 1982-08-11 | 光学活性なハ−フエステルの分離法 |
| DE8686112335T DE3382001D1 (de) | 1982-04-16 | 1983-04-15 | Verfahren zur herstellung optisch aktiver halbester. |
| EP86112335A EP0220435B1 (en) | 1982-04-16 | 1983-04-15 | A method for preparing optically active half esters |
| DE8383103665T DE3372365D1 (en) | 1982-04-16 | 1983-04-15 | Method of obtaining optically active half esters |
| EP83103665A EP0092194B1 (en) | 1982-04-16 | 1983-04-15 | Method of obtaining optically active half esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14029982A JPS5929670A (ja) | 1982-08-11 | 1982-08-11 | 光学活性なハ−フエステルの分離法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5929670A JPS5929670A (ja) | 1984-02-16 |
| JPH0435464B2 true JPH0435464B2 (ru) | 1992-06-11 |
Family
ID=15265552
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14029982A Granted JPS5929670A (ja) | 1982-04-16 | 1982-08-11 | 光学活性なハ−フエステルの分離法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5929670A (ru) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5592343A (en) * | 1979-01-06 | 1980-07-12 | Yoshio Katsuta | Preparation of optically active substituted isovaleric acid |
| JPS55118455A (en) * | 1979-03-02 | 1980-09-11 | Sumitomo Chem Co Ltd | Method of collecting optically active d-alpha-methyl-beta- mercapto propionic acid derivative |
| JPS55136245A (en) * | 1979-04-09 | 1980-10-23 | Sumitomo Chem Co Ltd | Optical resolution of alpha-isopropyl-p-chlorophenyl-acetic acid |
-
1982
- 1982-08-11 JP JP14029982A patent/JPS5929670A/ja active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5592343A (en) * | 1979-01-06 | 1980-07-12 | Yoshio Katsuta | Preparation of optically active substituted isovaleric acid |
| JPS55118455A (en) * | 1979-03-02 | 1980-09-11 | Sumitomo Chem Co Ltd | Method of collecting optically active d-alpha-methyl-beta- mercapto propionic acid derivative |
| JPS55136245A (en) * | 1979-04-09 | 1980-10-23 | Sumitomo Chem Co Ltd | Optical resolution of alpha-isopropyl-p-chlorophenyl-acetic acid |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5929670A (ja) | 1984-02-16 |
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