公开(公告)号：JPH09151159A

公开(公告)日：1997-06-10

申请号：JP31403995

申请日：1995-12-01

Applicant: TORAY INDUSTRIES

Inventor： IWATA SHIHO ,  NAKAI SAKIE ,  SATOU HARUYO

IPC: C07B55/00 ,  C07C51/347 ,  C07C57/58 ,  C07C59/50

Abstract: PROBLEM TO BE SOLVED: To obtain a racemic carboxylic acid useful as an intermediate raw material for medicines and agrochemicals in high yield by reducing the amount of a base used and racemizing an optically active carboxylic acid under mild conditions. SOLUTION: The racemizing reaction of an optically active carboxylic acid represented by the formula (R and R are each hydroxyl, a 1-10C alkyl, a 6-10C aryl, a 7-11C aralkyl or a 5-6C cycloalkyl; X is H or an alkali metal) or an alkali metallic salt thereof is carried out in the coexistence of a base (e.g. potassium hydroxide) and dimethyl sulfoxide at 60-130 deg.C for 0.1-40hr. The base is used in an amount of 1.01-10 equiv. based on the optically active carboxylic acid and 0.01-9 equiv. based on the alkali metallic salt of the optically active carboxylic acid. The dimethyl sulfoxide is used in an amount of 0.1-10 times based on the optically active carboxylic acid (alkali metallic salt). An organic solvent (e.g. cyclohexane) and water may coexist in racemization.

公开(公告)号：JPH07165702A

公开(公告)日：1995-06-27

申请号：JP34088493

申请日：1993-12-09

Applicant: TORAY INDUSTRIES

Inventor： ONO TAKAE ,  SATOU HARUYO ,  IMAMURA SHINZO

IPC: C07C403/20

Abstract: PURPOSE:To isolate a natural type abscisic acid being an important compound as a natural plant hormone and capable of expecting wide uses such as plant growth regrator, etc., in high purity and yield from a solution containing the natural type abscisic acid by carrying out the isolation operation of the natural type abscisic acid in a state in which light having a specific wavelength is blocked. CONSTITUTION:A natural type abscisic acid is isolated in high yield from a solution containing the natural type abscisic acid by carrying out isolation operation of the natural type abscisic acid in a state in which light having 200-600nm wavelength is blocked. This isolation is preferably carried out under conditions at pH1-11 and temperature of 0-60 deg.C. An >=80% of total isolation operation based on time is preferably carried out in a state in which light having 200-600nm wavelength is blocked. Furthermore, the natural type abscisic acid(ABA) is (+)-cis-trans type expressed by the formula. The isomerization and decomposition of ABA are suppressed and recovery of ABA is enhanced and ABA can efficiently be isolated by this method. Further, since the isolated ABA is not isolated or decomposed even in successive operation, high-purity ABA is readily obtained.

公开(公告)号：JPH06312975A

公开(公告)日：1994-11-08

申请号：JP10448993

申请日：1993-04-30

Applicant: TORAY INDUSTRIES

Inventor： ONO TAKAE ,  SATOU HARUYO

IPC: C07C403/20

Abstract: PURPOSE:To efficiently and selectively isolate abscisic acid from a dilute solution containing the abscisic acid in high yield without concentrating an organic layer extracted with an organic solvent by reducing the amount of the organic solvent used. CONSTITUTION:The method for isolating abscisic acid is characterized by comprising an extraction step for bringing an aqueous solution containing the abscisic acid into contact with an organic solvent immiscible with water and making the abscisic acid pass into the organic solvent, a back extraction step for bringing the organic layer, separated from the extraction step and containing the abscisic acid into contact with an aqueous solution of an alkali and making the abscisic acid pass into the aqueous solution of the alkali, a recycling step for recycling the organic layer subjected to the back extraction of the abscisic acid in the back extraction step to the extraction step and a step for isolating the abscisic acid from the aqueous solution of the alkali, separated in the back extraction step and containing the abscisic acid. The isolated abscisic acid is capable of reducing the subsequent purification load and providing an industrially inexpensive high-purity abscisic acid (ABA).

公开(公告)号：JPH0532620A

公开(公告)日：1993-02-09

申请号：JP18896791

申请日：1991-07-29

Applicant: TORAY INDUSTRIES

Inventor： ITO NORIKO ,  SATOU HARUYO

IPC: C07D207/12 ,  C07B57/00

Abstract: PURPOSE:To produce optically active 3-hydroxypyrrolidine by optically resolving easily available RS-3-hydroxypyrrolidine with an industrially easily available optically active tartaric acid anilide as a resolving agent. CONSTITUTION:RS-3-hydroxypyrrolidine (e.g. quantitatively obtained by reducing commercially available RS-N-benzyl-3-hydroxypyrrolidine in the presence of Pd/C catalyst) is optically resolved with an optically active tartaric acid anilide (both of the D and L isomers can be used) of the formula (R is chlorine or nitro) as a resolving agent to produce an optically active 3-hydroxypyrrolidine. The optically active tartaric acid anilide is obtained in a high yield e.g. by reacting tartaric acid with acetic anhydride, reacting the produced diacetyl tartaric acid anhydride with p-chloro or nitro-aniline and subsequently hydrolyzing the reaction product. The optically resolving agent is produced from inexpensive raw materials in a high yield, is chemically highly stable, can be recovered from a diastereomer salt solution in a high yield without being racemized, and can again be used.

公开(公告)号：JPH04149154A

公开(公告)日：1992-05-22

申请号：JP27500290

申请日：1990-10-11

Applicant: TORAY INDUSTRIES

Inventor： WAKABAYASHI YUKIO ,  MIYATA AKIRA ,  SATOU HARUYO

IPC: C07C67/343 ,  C07C69/738

Abstract: PURPOSE:To economically obtain the title compound in high yield without solidifying a reaction mixture by subjecting acetophenone and a dialkyl oxalate to condensing reaction in the presence of a sodium alkoxide using an organic solvent separable from water. CONSTITUTION:Acetophenone and a dialkyl oxalate are subjected to condensing reaction in the presence of a sodium alkoxide using an organic solvent (toluene, etc., are especially preferred) separable from water as a reaction solvent to afford a 2,4-dioxo-4-phenylbutyric acid ester. Since the fluidity of the reaction mixture is always kept according to the aforementioned method without causing trouble such as solidification, control in mass production is facilitated. Furthermore, since a high reaction concentration can be set, production efficiency is improved and the above-mentioned method is economically advantageous. Nearly quantitative high yield can further advantageously be attained.

公开(公告)号：JPH04108766A

公开(公告)日：1992-04-09

申请号：JP22735790

申请日：1990-08-28

Applicant: TORAY INDUSTRIES

Inventor： NAKAI SAKIE ,  SATOU HARUYO

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

Abstract: PURPOSE:To optically resolve (RS)-1-methyl-3-phenylpropylamine by extremely simple method and in good yield and in high optical purity, using an optically active N-formylphenylglycin as a resolving agent. CONSTITUTION:1mol (RS)-1-methyl-3-phenylpropylamine is brought into contact with 0.1-2.0mol, preferably 0.3-1.0mol N-formyl-D-phenylglycin or N-formyl-L- phenylglycin in a solvent, preferably water or ethanol to produce two kinds of diastereomer salts. The solution is cooled and/or concentrated to crystallize a hardly soluble diastereomer salt and the diastereomer is separated and collected according to an ordinary solid-liquid separation method. The separated diastereomer salt is treated with an acid or alkali. Thereby, optically active objective compound is obtained and simultaneously optically active N- formylphenylglycin is recovered and re-used.

公开(公告)号：JPH03112491A

公开(公告)日：1991-05-14

申请号：JP24883789

申请日：1989-09-25

Applicant: TORAY INDUSTRIES

Inventor： FUJIKAWA KAZUHIRO ,  SATOU HARUYO ,  YONEHARA TORU ,  MIYATA AKIRA

IPC: C12P13/22 ,  C12R1/01 ,  C12R1/06 ,  C12R1/13 ,  C12R1/15

Abstract: PURPOSE:To produce L-homophenylalanine useful as a raw material for a precursor of ACE inhibitor, having high optical purity, efficiently and inexpensively by treating benzyllactic acid with a culture mixture or cells of bacterium having specific action. CONSTITUTION:Benzyllactic acid (substrate concentration: about 0.1-5%) is aerobically treated with a culture mixture of a bacterium such as Corynebacterium glutamicum ATCC 13032 belonging to at least one of Corynebacterium, Brevibacterium, Bacillus, Microbacterium, Citrobacter and Arthrobacter or, capable of converting benzyllactic acid into L- homophenylalanine, or cells or treated material thereof at preferably 25-35 deg.C at pH7.5-9.5 and L-homophenylalanine is isolated from the reaction solution and collected.

公开(公告)号：JPH0265797A

公开(公告)日：1990-03-06

申请号：JP21414888

申请日：1988-08-29

Applicant: TORAY INDUSTRIES

Inventor： ITO NORIKO ,  SATOU HARUYO

IPC: C12P41/00 ,  C12R1/645

Abstract: PURPOSE:To efficiently obtain the subject compound capable of highly selectively assimilating only L-phenylalanine and useful as a pharmaceutical intermediate in a short time by culturing a specific microorganism in a DL-phenylalanine- containing culture medium. CONSTITUTION:A microorganism (e.g. Rhodosporidium.torulides ATCC10788), belonging to the genus Rhodotorula, Rhodosporidium or Providencia and having the ability to assimilate L-phenylalanine without assimilating D-phenylalanine is cultured in a DL-phenylalanine-containing culture medium and the objective compound is then isolated from the culture solution. Furthermore, the culture is preferably carried out by a flow addition culture method for dividedly adding the DL-phenylalanine.

公开(公告)号：JPS58150551A

公开(公告)日：1983-09-07

申请号：JP3294082

申请日：1982-03-02

Applicant: TORAY INDUSTRIES

Inventor： SATOU HARUYO ,  IMAMURA SHINZOU ,  OONO AKIRA

IPC: C07C227/04 ,  C07C67/00 ,  C07C227/00 ,  C07C227/06 ,  C07C229/22 ,  C07C241/00 ,  C07C251/24

Abstract: NEW MATERIAL:N-(Diphenylmethylene)serine expressed by formulaIand a salt thereof. USE:Useful as a synthetic intermediate for amino acids, and obtainable in high yield by easy operation. PROCESS:An alkyl ester of N-(diphenylmethylene)glycine expressed formula II (R is lower alkyl) is reacted with formaldehyde and/or paraformaldehyde preferably in a two-phase solvent system in the presence of a base, e.g. a carbonate, more preferably in the presence of a phase transfer catalyst, e.g. tetrabutylammonium hydrogensulfate or benzyltrimethylammonium hydroxide, at 0-80 deg.C, preferably 0-40 deg.C, under ordinary pressure for 5-120min to give the aimed compound expressed by formulaI.

公开(公告)号：JPS58116469A

公开(公告)日：1983-07-11

申请号：JP21381081

申请日：1981-12-28

Applicant: TORAY INDUSTRIES

Inventor： SATOU HARUYO ,  IMAMURA SHINZOU

IPC: C07D223/12

Abstract: NEW MATERIAL:The epsilon-caprolactam derivative of formulaI(R is H, lower alkyl or phenyl; phi is phenyl). EXAMPLE:alpha-Phenylmethyleneamino-epsilon-caprolactam. USE:Pharmaceuticals, agricultural chemicals, their intermediates, and intermediate of a dissolving agent (optically active alpha-mono-alkylamino-epsilon-caprolactam). PROCESS:The compound of formulaIcan be prepared by reacting alpha-amino-epsilon- caprolactam with the aromatic compound of formula II in the presence of a solvent such as benzene, toluene, etc. at 30-150 deg.C, preferably 50-110 deg.C. The compound of formulaI can be converted to a dissolving agent (alpha-monoalkylamino-epsilon-caprolactam) by alkylation followed by hydrolysis in the presence of an acid.