公开(公告)号：JPH0971577A

公开(公告)日：1997-03-18

申请号：JP22894395

申请日：1995-09-06

Applicant: TORAY INDUSTRIES

Inventor： NAKAI SAKIE ,  SATOU HARUYO

IPC: C07D307/24 ,  C07C27/02 ,  C07C51/02 ,  C07C51/04 ,  C07C51/083 ,  C07C51/56 ,  C07C51/60 ,  C07C67/14 ,  C07D309/08

Abstract: PROBLEM TO BE SOLVED: To isolate carboxylic acid or its ester which is useful as an intermediate for medicines or as a starting material for liquid crystal in high purity and high yield by bringing a salt of carboxylic acid into contact with a chlorinating agent to effect salt dissolution in a substantially water-free (anhydrous) organic solvent. SOLUTION: Preferably, in an alcohol solvent or in at least one of organic solvent selected from ethers, halogenated hydrocarbons and hydrocarbons containing an alcohol, (A) a salt of carboxylic acid, [(R)-tetrahydrofuran-2- carboxylic acid.L-phenylalanineamide salt or the like] is brought into contact with (B) a chlorinating agent, preferably thionyl chloride and/or phosgene at 0 deg.C to 50 deg.C to give the objective carboxylic acid or its derivative. It is preferred that the solubility of the carboxylic acid in water is >=10g/100g of water at 25 deg.C and the solubility in the organic solvent is >=5g/100g of the organic solvent at 25 deg.C.

公开(公告)号：JPH0971571A

公开(公告)日：1997-03-18

申请号：JP17089296

申请日：1996-07-01

Applicant: TORAY INDUSTRIES

Inventor： FUJINO TOSHIHIRO ,  SATOU HARUYO

IPC: C07D241/04 ,  C07B57/00 ,  C07C233/46 ,  C07C233/83 ,  C07C271/22 ,  C07C311/04 ,  C07C311/06 ,  C07C311/08

Abstract: PROBLEM TO BE SOLVED: To obtain an optically active 2-piperazinecarboxylic acid derivative useful as an intermediate for medicines, etc., in a high optical purity and in a high yield by employing the chemically modified derivative of an inexpensively available optically active amino acid as an optical revolving agent. SOLUTION: An optically active 2-piperazinecarboxylic acid derivative is obtained by bringing 1 mole of a 2-piperazinecarboxylic acid derivative into contact with 0.4-1.2 moles, especially 0.5-1.0mole, of an optical resolving agent in a solvent. The optical resolving agent is preferably selected from an optically active N-acylamino acid derivative of formula I (R is a 1-10C alkyl which may not be substituted or may be substituted with a hydroxyl group, a carboxyl group, etc., an aryl which may be substituted or may be substituted with a 1-10C alkyl, etc.) and an optically active N-sulfonylamino acid derivative of formula II (R is a 1-10C alkyl which may not be substituted or may be substituted with a carboxyl or carbamoyl group, etc.; R is a 1-10C alkyl, an aryl which may not be substituted or may be substituted with a 1-10C alkyl, etc.).

公开(公告)号：JPH06107602A

公开(公告)日：1994-04-19

申请号：JP26042392

申请日：1992-09-30

Applicant: TORAY INDUSTRIES

Inventor： NAKAI SAKIE ,  SATOU HARUYO

IPC: C07B57/00 ,  C07C209/88 ,  C07C211/27

Abstract: PURPOSE:To optically resolve (RS)-1-phenylethylamine in high yield and in high optical purity by using a specific resolving agent such as optically active N-formylphenylglycine obtainable from an inexpensive raw material and reusable. CONSTITUTION:(RS)-1-Phenylethylamine is optically resolved by using a compound selected from optically active N-formylphenylglycine, an optically active tartaric acid anilide derivative of the formula (R is methoxy or nitro) and optically active N-benzoylmethionine as an optically resolving agent to give optically active 1-formylphenylamine. The resolving agent such as optically active N-p-nitrobenzoylalanine is obtained in high yield by reacting a basic aqueous solution of alanine with p-nitrobenzoyl chloride and precipitating with an acid. The resolving agents used are slightly soluble, can be recovered from a solution of diastereomer salt in high yield and decomposition and racemization hardly occur in the recovery process.

公开(公告)号：JPH0418084A

公开(公告)日：1992-01-22

申请号：JP11949590

申请日：1990-05-08

Applicant: TORAY INDUSTRIES

Inventor： NAKAI SAKIE ,  SATOU HARUYO

IPC: C07D295/02 ,  C07B57/00 ,  C07D241/04

Abstract: PURPOSE:To easily produce the subject compound useful as an intermediate for pharmaceuticals such as quinolone antibacterial agent in high optical purity by carrying out the optical resolution of (RS)-methylpiperazine using an optically active N-substituted phenylglycine as an optical resolution agent. CONSTITUTION:The objective compound can be produced by the optical resolution of (RS)-2-methylpiperazine using an optically active N-substituted phenylglycine of formula (R is benzoyl or p-toluenesulfonyl) as an optical resolution agent. The optical resolution is preferably carried out by contacting 1mol of (RS)-2-methylpiperazine with 0.3-1.0mol of N-substituted phenylglycine in a solvent.

公开(公告)号：JPH03153648A

公开(公告)日：1991-07-01

申请号：JP29293189

申请日：1989-11-10

Applicant: TORAY INDUSTRIES

Inventor： HASEGAWA SAKIE ,  SATOU HARUYO

IPC: C07C209/88 ,  C07C211/27

Abstract: PURPOSE:To obtain the title optically active substance useful as a raw material for drugs such as beta-blocker by a simple method in high yield by optically resolving (RS)-1-methyl-3-phenylpropylamine with optically active pantolactone as a resolving agent. CONSTITUTION:Optically active pantolactone is used as a resolving agent, for example, (RS)-1-methyl-3-phenylpropylamine is brought into contact with 0.1-2.0mol, preferably 0.5-10mol based on 1mol of the compound of the resolving agent in a solvent such as lower alcohol, acetone or ethyl acetate, the prepared diastereomer salt is separated, decomposed into the resolving agent and optically active 1-methyl-3-phenylpropylamine to give the optically active substance at an industrially realizable level. The resolving agent is readily recovered by treating the diastereomer salt with an acid or an alkali and can be reused.

公开(公告)号：JPH02121950A

公开(公告)日：1990-05-09

申请号：JP27386688

申请日：1988-10-28

Applicant: TORAY INDUSTRIES

Inventor： MIYATA AKIRA ,  SATOU HARUYO

IPC: B01J31/04 ,  C07B55/00 ,  C07B61/00 ,  C07C67/30 ,  C07C67/31 ,  C07C69/732

Abstract: PURPOSE:To easily obtain the subject compound without using expensive reagent by treating an optically active a alpha-sulfonyloxyacid ester with a fatty acid sodium salt, etc., in a lower alcohol and treating the product with an acid, thereby inverting the steric configuration of the starting compound. CONSTITUTION:An optically active a alpha-sulfonyloxyacid ester of formula I (Rl is lower alkyl, R2 is lower alkyl or aryl; represents asymmetric carbon) is treated with at least one kind of salt selected from sodium or potassium salt of a 1-3C fatty acid (especially preferably sodium acetate or potassium acetate) under heating at 10-150 deg.C, preferably 20-120 deg.C and the product is treated with an acid or a weak base to obtain the objective compound of formula II having inverted steric configuration. The amount of the treating agent for the 2nd treatment process is preferably 1.1-2.0 equivalent in the case of an acid or a catalytic amount in the case of a weak base.

公开(公告)号：JPH0253755A

公开(公告)日：1990-02-22

申请号：JP20216688

申请日：1988-08-12

Applicant: TORAY INDUSTRIES

Inventor： HASEGAWA SAKIE ,  SATOU HARUYO

IPC: C07C209/88 ,  C07B57/00 ,  C07C67/00 ,  C07C209/00 ,  C07C211/27

Abstract: PURPOSE:To optically resolve (R S)-1-methyl-3-phenylpropylamine through a diastereomeric salt in extremely simple method, good yield and high optical purity using an optically active N-benzoylphenylglycine as a resolving agent. CONSTITUTION:(R S)-1-Methyl-3-phenylpropylamine is reacted with an optically active N-benzoylphenylglycine used as a resolving agent to give two kind of diastereomeric salts and (R S)-1-methyl-3-phenylpropylamine is then subjected to optical resolution utilizing the difference between the diastereomeric salts to provide the optically active 1-methyl-3-phenylpropylamine useful as a raw material for a medicine such as beta-blocker in high yield and purity. Furthermore, the above-mentioned resolving agent can be readily recovered by treating the diastereomeric salt with an acid or alkali and reused.

公开(公告)号：JPH023627A

公开(公告)日：1990-01-09

申请号：JP14533788

申请日：1988-06-13

Applicant: TORAY INDUSTRIES

Inventor： HASEGAWA SAKIE ,  SATOU HARUYO

IPC: C07C209/88 ,  C07B57/00 ,  C07C67/00 ,  C07C209/00 ,  C07C211/27

Abstract: PURPOSE:To easily obtain the subject compound useful as a synthetic raw material for pharmaceuticals in high yield and optical purity by the optical resolution of (RS)-1-metyl-3-phenyl-propylamine with optically active N- acylmethione as a resolution agent. CONSTITUTION:The objective compound useful as a synthetic raw material for pharmaceuticals such as beta-blocker is produced by contacting 1mol of (RS)-1- methyl-3-phenylpropylamine with 0.1-2.0mol of optically active N-acrylmethionine of formula (R is phenyl or CH3) as a resolution agent in a solvent (e.g., water) to effect the optical resolution, cooling and/or concentrating the obtained solution to crystallize a hardly soluble diastereomer salt usually at 0-80 deg.C and easily separating the objective compound using conventional solid-liquid separation process. The compound of formula used as the resolution agent can be easily recovered by treating the diastereomer salt with an acid and an alkali and the recovered optically active N-acylmethionine can be reused.

公开(公告)号：JPS63198997A

公开(公告)日：1988-08-17

申请号：JP2970987

申请日：1987-02-13

Applicant: TORAY INDUSTRIES

Inventor： ITO NORIKO ,  IMAMURA SHINZO ,  SATOU HARUYO

IPC: C12P13/06 ,  C12P41/00 ,  C12R1/645 ,  C12R1/72 ,  C12R1/78 ,  C12R1/84 ,  C12R1/85 ,  C12R1/88

Abstract: PURPOSE:To obtain D-alanine useful as an intermediate for drugs or an intermediate for sweeteners efficiently, by cultivating specific yeast in a medium containing DL-alanine. CONSTITUTION:Yeast belonging to the genus Candida, Saccharomycospsis, Pichia, Torulopsis, Cryptococcus, Hansenula or Torycosporon, capable of assimilating L-alanine but substantially not D-alanine, is cultivated in a medium containing DL-alanine as a single carbon source and a single nitrogen source and D-alanine is collected from the culture mixture. Candida humicola ATCC36992, etc., may be cited as the yeast.

公开(公告)号：JPS6032772A

公开(公告)日：1985-02-19

申请号：JP13763383

申请日：1983-07-29

Applicant: TORAY INDUSTRIES

Inventor： FUJII SUNAO ,  IMAMURA SHINZOU ,  SATOU HARUYO

IPC: C07D211/76

Abstract: PURPOSE:To obtain the titled compound useful as a compound convertible to ornithine, one of alpha-amino acids, without using ornithine as a starting raw material, by reacting 2-cyanoethylglycine ester with hydrogen in the presence of a catalyst. CONSTITUTION:2-Cyanoethylglycine ester as a raw material is reacted with hydrogen in the presence of a nickel-type and/or cobalt-type catalyst at 10-100 deg.C, especially preferably at 15-50 deg.C at 1-500atm., preferably >=10atm., to give the desired compound. Especially Raney cobalt is preferable as the catalyst, and an amount of it used is 1-50wt%, especially preferably 2.5-20wt% calculated as catalyst metal based on the raw material. 2-Cyanoethylglycine ester as the raw material, for example, is synthesized by subjecting acrylonitrile to Michael addition to a Schiff base of glycine ester and benzophenone, hydrolyzing the addition product in the presence of an acid.