JPH0153665B2 - - Google Patents
Info
- Publication number
- JPH0153665B2 JPH0153665B2 JP56127864A JP12786481A JPH0153665B2 JP H0153665 B2 JPH0153665 B2 JP H0153665B2 JP 56127864 A JP56127864 A JP 56127864A JP 12786481 A JP12786481 A JP 12786481A JP H0153665 B2 JPH0153665 B2 JP H0153665B2
- Authority
- JP
- Japan
- Prior art keywords
- mandelonitrile
- optically active
- benzaldehyde
- reaction
- hydrogen cyanide
- 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
- NNICRUQPODTGRU-UHFFFAOYSA-N mandelonitrile Chemical compound N#CC(O)C1=CC=CC=C1 NNICRUQPODTGRU-UHFFFAOYSA-N 0.000 claims description 40
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 28
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 22
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 14
- 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 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 230000003287 optical effect Effects 0.000 description 9
- 239000007788 liquid Substances 0.000 description 5
- 229960002510 mandelic acid Drugs 0.000 description 5
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 4
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- NNICRUQPODTGRU-QMMMGPOBSA-N (R)-mandelonitrile Chemical compound N#C[C@H](O)C1=CC=CC=C1 NNICRUQPODTGRU-QMMMGPOBSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229960002885 histidine Drugs 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000011982 enantioselective catalyst Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- IWYDHOAUDWTVEP-SSDOTTSWSA-N (R)-mandelic acid Chemical compound OC(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-N 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- 101000874334 Dalbergia nigrescens Isoflavonoid 7-O-beta-apiosyl-glucoside beta-glycosidase Proteins 0.000 description 1
- 108010016626 Dipeptides Proteins 0.000 description 1
- 101000757733 Enterococcus faecalis (strain ATCC 700802 / V583) Autolysin Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
- 101000757734 Mycolicibacterium phlei 38 kDa autolysin Proteins 0.000 description 1
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical class C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- OLVCFLKTBJRLHI-AXAPSJFSSA-N cefamandole Chemical compound CN1N=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)[C@H](O)C=3C=CC=CC=3)[C@H]2SC1 OLVCFLKTBJRLHI-AXAPSJFSSA-N 0.000 description 1
- 229960003012 cefamandole Drugs 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12786481A JPS5829757A (ja) | 1981-08-17 | 1981-08-17 | 光学活性マンデロニトリルの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12786481A JPS5829757A (ja) | 1981-08-17 | 1981-08-17 | 光学活性マンデロニトリルの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5829757A JPS5829757A (ja) | 1983-02-22 |
| JPH0153665B2 true JPH0153665B2 (da) | 1989-11-15 |
Family
ID=14970537
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12786481A Granted JPS5829757A (ja) | 1981-08-17 | 1981-08-17 | 光学活性マンデロニトリルの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5829757A (da) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4582646A (en) * | 1982-11-22 | 1986-04-15 | Shell Oil Company | Preparation of cyanomethyl esters |
| US4723027A (en) * | 1982-11-22 | 1988-02-02 | E. I. Du Pont De Nemours And Company | Preparation of optically active alpha-hydroxynitriles |
| US4560515A (en) * | 1982-11-22 | 1985-12-24 | Shell Oil Company | Preparation of optically-active cyanomethyl esters |
| NZ206106A (en) * | 1982-11-22 | 1987-10-30 | Shell Oil Co | Processes for the preparation of optically active cyanomethyl esters of alpha-chiral carboxylic acids and optionally substituted s-alpha-cyano-3-phenoxybenzyl alcohol |
| ZA837994B (en) * | 1982-11-22 | 1984-06-27 | Shell Oil Co | Process for the preparation of optically-active cyanomethyl esters |
| US4554102A (en) * | 1983-09-26 | 1985-11-19 | Shell Oil Company | Cyanohydrination catalyst comprising non-crystalline or amorphous dipeptide |
| US4569793A (en) * | 1984-09-26 | 1986-02-11 | Shell Oil Company | Cyanohydrination catalyst |
| US4611077A (en) * | 1985-06-26 | 1986-09-09 | Shell Oil Company | Increasing enantiomeric selectivity in chiral cyanohydrination |
| US4611076A (en) * | 1985-06-26 | 1986-09-09 | Shell Oil Company | Chiral cyanohydrination process |
-
1981
- 1981-08-17 JP JP12786481A patent/JPS5829757A/ja active Granted
Non-Patent Citations (2)
| Title |
|---|
| JOURNAL OF THE CHEMICAL SOCIETY=1981 * |
| MAKROMOL CHEM=1979 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5829757A (ja) | 1983-02-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0153665B2 (da) | ||
| Shi et al. | Ethyl 3-Fluoro-3-(tributylstannyl)-2-methoxyacrylate: Preparation and Palladium/Copper-Cocatalyzed Cross-Coupling Reactions as a Novel Route to. beta.-Fluoro-. alpha.-keto Acid Derivatives | |
| Ukaji et al. | Asymmetric Bis (alkoxycarbonylation) Reaction of Homoallylic Alcohols Catalyzed by Palladium in the Presence of Cu (I) Triflate Using the Chiral Bioxazoline Ligand. | |
| CN113072456B (zh) | 一种手性α-二氟甲基氨基酸类化合物及其制备方法 | |
| US6476250B1 (en) | Optically active fluorinated binaphthol derivative | |
| Sauriol-Lord et al. | Asymmetric induction in additions to epoxides. Addition of. alpha.-anions of N, N-disubstituted carboxamides | |
| KR100387932B1 (ko) | 키랄 의약품의 광학분할을 위한 lc 용 키랄 크라운 에테르 키랄 고정상 및 이들로 충진된 키랄 칼럼 | |
| JP4308155B2 (ja) | δ−イミノマロン酸誘導体の製造方法、及びそのための触媒 | |
| JPH01233255A (ja) | シクロペンテノン誘導体及びその製造法 | |
| JP3547590B2 (ja) | 不斉ジルコニウム触媒 | |
| CN116891405B (zh) | 一种手性α，α-二芳基酮类化合物及其制备方法和应用 | |
| JP2862962B2 (ja) | トランス―メチルヘキサヒドロ無水フタル酸の製造方法 | |
| JP2625204B2 (ja) | α，α‐ジハロケトンの製造法 | |
| JPS62212352A (ja) | カルニチン中間体の製造方法 | |
| KR100461571B1 (ko) | 고순도 (ｓ)-1,2,4-부탄트리올의 제조방법 | |
| JPS5944303B2 (ja) | α−ケトアシド類の製造法 | |
| Yonezawa et al. | Synthesis of New 2-Oxazolinones from N-Carboxy α-Dehydroamino Acid Anhydrides | |
| CN118530134A (zh) | 一种含亚烷基轴向手性亚胺酸酯类化合物的合成方法 | |
| CN118930472A (zh) | 一种3-氯-2-甲醛吲哚衍生物的制备方法 | |
| JP2831776B2 (ja) | 異性体分離法 | |
| JP2005232103A (ja) | 光学活性なビシナルジアミンおよびその製造方法 | |
| JPS61176580A (ja) | 光学活性３，４−エポキシ−１−ブタノ−ルの製法 | |
| JPH08198818A (ja) | ニトロオレフィンの製造方法 | |
| JPH06122654A (ja) | 高光学純度のβ，β，β−トリフルオロ乳酸エステル化合物の製造方法 | |
| JPH05112518A (ja) | 光学活性シアノヒドリン類の高効率製造法 |