公开(公告)号：JPH10218863A

公开(公告)日：1998-08-18

申请号：JP33522697

申请日：1997-12-05

Applicant: TORAY INDUSTRIES

Inventor： FUJINO TOSHIHIRO ,  SATOU HARUYO

IPC: C07D241/04 ,  C07B57/00

Abstract: PROBLEM TO BE SOLVED: To obtain the subject compound useful as an intermediate for medicines by a method high in the recovery of a resolving agent and in production efficiency by using an optically active acidic amino acid derivative as the resolving agent. SOLUTION: The mixture of a (+)-2-piperazinecarboxylic acid derivative with (-)-2-piperazinecarboxylic acid derivative as a raw material is brought into contact with a resolving agent such as an optically active N-acyl acidic amino derivative of the formula [R is H, a 1-10C alkyl; (n) is 1, 2] in an amount of 0.4-1.1 mole per mole of the raw material to produce the diastereoisomer salt. The obtained diastereoisomer salt is usually deposited from the solution at 0-100 deg.C, and the deposited salt is disintegrated to separate the optically active (+)-2-piperazinecarboxylic acid derivative, etc., from the resolving agent.

公开(公告)号：JPH07138206A

公开(公告)日：1995-05-30

申请号：JP31453093

申请日：1993-11-19

Applicant: TORAY INDUSTRIES

Inventor： FUJINO TOSHIHIRO

IPC: C07C51/087 ,  C07C57/38 ,  C07C67/28 ,  C07C69/76

Abstract: PURPOSE:To obtain an O, O'-diacyltartaric acid crystal in good operability and high yield without producing a bulk material by hydrolyzing an O, O'- diacyltartaric anhydride in water in the presence of an organic solvent immiscible with water. CONSTITUTION:An O, O'-diacyltartaric anhydride of formula I (R and R are each H, a halogen or a 1-3C alkyl) is hydrolyzed in water in the presence of an organic solvent immiscible with water to obtain the objective O, O'- diacyltartaric acid of formula II. As the organic solvent added, especially benzene, toluene, xylene or chlorobenzene is preferably used. The organic solvent is preferably added in an amount of 0.01-0.5 time by weight based on the compound of formula I. The optically active O, O'-diacyltartaric acid is useful as an optically resolving agent for various racemic amines. According to this method, this compound of formula 1 can be produced in a high yield and good operability without causing troubles, e.g. a trouble incapable of taking out O, O'-diacyltartaric acid hydrate from a reactor owing to attaching the hydrate to a wall of the reactor or stirrer, etc., in crystallization.

公开(公告)号：JPS6445349A

公开(公告)日：1989-02-17

申请号：JP20212587

申请日：1987-08-13

Applicant: TORAY INDUSTRIES

Inventor： ONO TAKAE ,  MORITA SHOJI ,  FUJINO TOSHIHIRO

IPC: C07C229/26

Abstract: PURPOSE:To obtain DL-lysine useful as a basic salt-forming agent for an acidic drug such as aspirin, with economical means in high purity, by racemizing an optically active lysine and treating with a free acid. CONSTITUTION:1mol. (2 equivalent) of an optically active lysine is racemized at 130-200 deg.C by using 0.4-5 times weight of water in the presence of 1-2 equivalent of an acid (e.g. hydrochloric acid). To improve the quality of the product, the racemization reaction liquid is added with 2.1-3 equivalent [based on 1mol. (2 equivalent) of lysine] of an acid (e.g. hydrochloric acid) and treated with the acid at 120-180 deg.C. If necessary, the reaction product is subjected to activated carbon treatment for removing coloring impurities, ion exchange treatment to remove the acid and obtain free DL-lysine, etc.

公开(公告)号：JP2002255902A

公开(公告)日：2002-09-11

申请号：JP2001050020

申请日：2001-02-26

Applicant: TORAY INDUSTRIES

Inventor： FUJINO TOSHIHIRO ,  SATO HARUYO

IPC: C07C71/00 ,  C07B63/00

Abstract: PROBLEM TO BE SOLVED: To chemically purify a thermally unstable optically active carboxylic acid chloride without accompanying racemization. SOLUTION: This method of purification for the optically active carboxylic acid chloride distills the optically active carboxylic acid chloride, preferably the optically active carboxylic acid chloride expressed by general formula 1 (R is a 1-8C alkyl group, a 1-4C alkoxyl group, a hydroxy group esterified by a 1-4C aliphatic acid, a substituted phenyl group, an aralky group having a (substituted) phenyl group. * means that the symmetric carbon is optically active.), using a thin film evaporator or a molecular distillation system.

公开(公告)号：JP2002255893A

公开(公告)日：2002-09-11

申请号：JP2001050019

申请日：2001-02-26

Applicant: TORAY INDUSTRIES

Inventor： FUJINO TOSHIHIRO ,  SATO HARUYO

IPC: C07C51/64 ,  C07C59/255

Abstract: PROBLEM TO BE SOLVED: To provide a method for stably storing an aqueous solution of an optically active tartaric acid salt produced by microbial reaction. SOLUTION: An aqueous solution of an optically active tartaric acid salt produced by microbial reaction is heat-treated at >=80 deg.C after completing the culture. Concretely, an aqueous solution of D-tartaric acid obtained by culturing a microbial strain of the genus Pseudomonas in a solution of DL-tartaric acid is heat-treated at >=80 deg.C or stably stored in an anaerobic atmosphere after the heat-treatment.

公开(公告)号：JP2002234873A

公开(公告)日：2002-08-23

申请号：JP2001279111

申请日：2001-09-14

Applicant: TORAY INDUSTRIES

Inventor： FUJINO TOSHIHIRO ,  SATO HARUYO

IPC: C07D211/24 ,  A61K31/451 ,  A61P25/16 ,  C07B55/00 ,  C07B61/00

Abstract: PROBLEM TO BE SOLVED: To efficiently racemize a piperidine derivative such as 3-[3-(methylsulfonyl)phenyl]-1-propylpiperidine. SOLUTION: The objective method comprises reaction of an optically active piperidine derivative such as optically active 3-[3-(methylsulfonyl)phenyl]-1- propylpiperidine in the presence of a reducing catalyst in a hydrogen atmosphere; wherein it is preferable that the reducing catalyst contains a group VIII metal such as platinum and the hydrogen atmosphere is a pressure system with 0.2 MPa or greater.

公开(公告)号：JPH0859517A

公开(公告)日：1996-03-05

申请号：JP13462295

申请日：1995-06-01

Applicant: TORAY INDUSTRIES

Inventor： NAKAI SAKIE ,  SATOU HARUYO ,  FUJINO TOSHIHIRO

IPC: C07D307/24 ,  C07B57/00

Abstract: PURPOSE: To enable a practically advantageous production of optically active tetrahydrofurancarboxylic acid which is useful as an intermediate for medicines by using a chemically modified optically active amino acid inexpensively available as an agent for optical resolution. CONSTITUTION: An agent for optical resolution of tetrahydrofurancarboxylic acid, that is, an optically active amino acid amide. The agents of formula I or formula II (R1 is an alkyl, an aryl, an aralkyl; R2 , R3 are each an alkyl, an aryl, an aralkyl; R4 is a cyclic alkylamine residue) are preferred. The agent is used to effect the optical resolution to give optically active tetrahydrofuran- carboxylic acid. As an optically active amino acid amide derivative, is cited particularly optically active alanine benzyl-amide, optically active alanine anilide, optically active phenyl-alanine amide or the like. As the tetrahydrofurancarboxylic acid. tetrahydrofuran-2-carboxylic acid is particularly desirable. This agent for optical resolution can be used repeatedly.

公开(公告)号：JPH07138247A

公开(公告)日：1995-05-30

申请号：JP31456393

申请日：1993-11-19

Applicant: TORAY INDUSTRIES

Inventor： FUJINO TOSHIHIRO ,  SATOU HARUYO

IPC: C07D307/56 ,  B01J27/06 ,  C07B61/00

Abstract: PURPOSE:To produce O,O'-diacyltartaric acid anhydride in high purity and yield at a low cost by reacting a specific aromatic carboxylic acid with tartaric acid in the presence of a chlorinating agent and a catalyst. CONSTITUTION:The objective O,O'-diacyltartaric acid anhydride of formula II can be produced by reacting (A) an aromatic carboxylic acid of formula I (R and R are H, a halogen or a 1-3C alkyl) with (B) tartaric acid in the presence of (C) a chlorinating agent (preferably thionyl chloride) and (D) a catalyst (preferably a Lewis acid selected from ferric chloride, zinc chloride, aluminum chloride and boron trifluoride) at 40-170 deg.C (preferably 60-150 deg.C). The molar ratio of the component A to the component B is 1.8-4, preferably 2.0-2.4 and that of the component C to the component A is 1.4-3, preferably 1.5-2.0. The amount of the component D is 0.001-0.2mol, preferably 0.002-0.10mol based on 1mol of the component B.

公开(公告)号：JPH07138246A

公开(公告)日：1995-05-30

申请号：JP31447793

申请日：1993-11-19

Applicant: TORAY INDUSTRIES

Inventor： FUJINO TOSHIHIRO ,  SATOU HARUYO

IPC: C07D307/56 ,  B01J27/12 ,  C07B61/00

Abstract: PURPOSE:To obtain a colorless O,O'-diacyltartaric acid anhydride in high quality and yield by reacting a specific aromatic carboxylic acid chloride with tartaric acid using boron trifluoride as a catalyst. CONSTITUTION:The objective O,O'-diacyltartaric acid anhydride of formula II is produced by reacting (A) an aromatic carboxylic acid chloride of formula I (R and R are H, a halogen or a 1-3C alkyl) with (B) tartaric acid in the presence of (C) boron trifluoride as a catalyst. An aromatic carboxylic acid anhydride of formula III may be used as a substitute for the component A. The reaction is preferably carried out in the presence of thionyl chloride.

公开(公告)号：JPS6226261A

公开(公告)日：1987-02-04

申请号：JP16476285

申请日：1985-07-25

Applicant: TORAY INDUSTRIES

Inventor： FURUYA MASAAKI ,  FUJINO TOSHIHIRO ,  NAKAOKA KENJI

IPC: C07C271/54 ,  C07C67/00 ,  C07C239/00

Abstract: PURPOSE:To obtain at low cost a high-quality compound useful as a raw material for peptide synthesis, by reacting D- or L-N -benzyloxycarbonyllysine with t-butylphenyl carbonate. CONSTITUTION:D- Or L-N -benzyloxycarbonyllysine is reacted with 6-butylphenyl carbonate in a polar organic solvent such as dimethyl sulfoxide, etc., in the presence of an alkali metal such as hydroxide, carbonate, bicarbonate, etc., of an alkali metal such as K, Na, Li, etc., at 50-100 deg.C to give the aimed substance. The amount of the alkali metallic compound is 1.0-1.2 equivalent based on D- or L-lysine as the starting substance, the amount of t-butylphenyl carbonate is 1.0-1.5mol and the reaction is carried out.