JPH0435463B2 - - Google Patents
Info
- Publication number
- JPH0435463B2 JPH0435463B2 JP57104585A JP10458582A JPH0435463B2 JP H0435463 B2 JPH0435463 B2 JP H0435463B2 JP 57104585 A JP57104585 A JP 57104585A JP 10458582 A JP10458582 A JP 10458582A JP H0435463 B2 JPH0435463 B2 JP H0435463B2
- Authority
- JP
- Japan
- Prior art keywords
- optically active
- dibenzyl
- ethoxycarbonyl
- carboxylic acid
- oxoimidazolidine
- 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 35
- 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 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 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 claims description 4
- 239000000243 solution Substances 0.000 description 22
- 238000000034 method Methods 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 230000003287 optical effect Effects 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000013078 crystal Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 150000002596 lactones Chemical class 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 5
- 238000011081 inoculation Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 239000012456 homogeneous solution Substances 0.000 description 3
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- -1 Dibenzyl-5-ethoxycarbonyl-2-oxoimidazolidine-4-carboxylic acid Chemical compound 0.000 description 2
- 239000012448 Lithium borohydride Substances 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
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229960002685 biotin Drugs 0.000 description 2
- 235000020958 biotin Nutrition 0.000 description 2
- 239000011616 biotin Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FMBMNSFOFOAIMZ-GFCCVEGCSA-N (2r)-2-amino-1,1-diphenylpropan-1-ol Chemical compound C=1C=CC=CC=1C(O)([C@H](N)C)C1=CC=CC=C1 FMBMNSFOFOAIMZ-GFCCVEGCSA-N 0.000 description 1
- WIVKAHXCBJSNDF-IYBDPMFKSA-N (3as,6ar)-1,3-dibenzyl-3a,6a-dihydrofuro[3,4-d]imidazole-2,4,6-trione Chemical compound N1([C@@H]2[C@H](N(C1=O)CC=1C=CC=CC=1)C(=O)OC2=O)CC1=CC=CC=C1 WIVKAHXCBJSNDF-IYBDPMFKSA-N 0.000 description 1
- OIYMUIUXMYAXIX-UHFFFAOYSA-N 1,1-diphenylpropan-1-ol Chemical compound C=1C=CC=CC=1C(O)(CC)C1=CC=CC=C1 OIYMUIUXMYAXIX-UHFFFAOYSA-N 0.000 description 1
- MHUXPSIRIWIGJV-UHFFFAOYSA-N 1-ethoxycarbonyl-2-oxoimidazolidine-4-carboxylic acid Chemical compound CCOC(=O)N1CC(C(O)=O)NC1=O MHUXPSIRIWIGJV-UHFFFAOYSA-N 0.000 description 1
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical group ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application 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
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229960002179 ephedrine Drugs 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- DWRDBJCTLDOPFZ-UHFFFAOYSA-N imidazole-2,4-dione Chemical compound O=C1NC(=O)N=C1 DWRDBJCTLDOPFZ-UHFFFAOYSA-N 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10458582A JPS58222068A (ja) | 1982-06-16 | 1982-06-16 | 光学活性なシス−１，３−ジベンジル−５−エトキシカルボニル−２−オキソイミダゾリジン−４−カルボン酸の製造方法 |
| DE8686112335T DE3382001D1 (de) | 1982-04-16 | 1983-04-15 | Verfahren zur herstellung optisch aktiver halbester. |
| EP83103665A EP0092194B1 (en) | 1982-04-16 | 1983-04-15 | Method of obtaining optically active half esters |
| 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 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10458582A JPS58222068A (ja) | 1982-06-16 | 1982-06-16 | 光学活性なシス−１，３−ジベンジル−５−エトキシカルボニル−２−オキソイミダゾリジン−４−カルボン酸の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58222068A JPS58222068A (ja) | 1983-12-23 |
| JPH0435463B2 true JPH0435463B2 (fi) | 1992-06-11 |
Family
ID=14384508
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10458582A Granted JPS58222068A (ja) | 1982-04-16 | 1982-06-16 | 光学活性なシス−１，３−ジベンジル−５−エトキシカルボニル−２−オキソイミダゾリジン−４−カルボン酸の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58222068A (fi) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57198098A (en) * | 1981-05-29 | 1982-12-04 | Sagami Chem Res Center | Preparation of optically active monoester monocarboxylic acid |
-
1982
- 1982-06-16 JP JP10458582A patent/JPS58222068A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57198098A (en) * | 1981-05-29 | 1982-12-04 | Sagami Chem Res Center | Preparation of optically active monoester monocarboxylic acid |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58222068A (ja) | 1983-12-23 |
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