Patents Assigned to Rhodia Chirex, Inc.
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Patent number: 6960680Abstract: A process for making a water-soluble ?-hydroxynitrile. A 1,2-epoxide and an inorganic cyanide salt are reacted in a solvent having aqueous methanol and a buffer therein to form ?-hydroxynitrile. The buffer substantially inhibits the formation of reaction products other than ?-hydroxynitrile. Optionally, water may be removed from the ?-hydroxynitrile by azeotropic distillation with acetonitrile and subsequently purified via vacuum distillation and filtration.Type: GrantFiled: January 8, 2003Date of Patent: November 1, 2005Assignee: Rhodia Chirex, Inc.Inventors: Carl Henry Behrens, James Joseph Mencel
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Publication number: 20040214878Abstract: A process for producing enantiomerically enriched (S)-&agr;-(2-chlorophenyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-acetic acid hydrocarbyl ester, represented by the formula: 1Type: ApplicationFiled: April 23, 2003Publication date: October 28, 2004Applicant: Rhodia ChiRex, Inc.Inventor: Richard A. Silva
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Publication number: 20040133029Abstract: A process for making a water-soluble &bgr;-hydroxynitrile. A 1,2-epoxide and an inorganic cyanide salt are reacted in a solvent having aqueous methanol and a buffer therein to form &bgr;hydroxynitrile. The buffer substantially inhibits the formation of reaction products other than &bgr;hydroxynitrile. Optionally, water may be removed from the &bgr;hydroxynitrile by azeotropic distillation with acetonitrile and subsequently purified via vacuum distillation and filtration.Type: ApplicationFiled: January 8, 2003Publication date: July 8, 2004Applicant: Rhodia ChiRex, Inc.Inventors: Carl Henry Behrens, James Joseph Mencel
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Patent number: 6693206Abstract: The present invention provides a process for the preparation of an enantiomerically enriched non-racemic chiral diol and an enantiomerically enriched non-racemic chiral epoxy compound by a hydrolytic kinetic resolution reaction. The process includes the step of contacting oxygen and mixture including a racemic chiral epoxy compound, a non-racemic Co(II) complex catalyst, an aromatic carboxylic acid and water, at a temperature and length of time sufficient to produce a mixture of said non-racemic chiral diol and said non-racemic chiral epoxy compound. The present invention also provides a process for the preparation of an enantiomerically enriched non-racemic chiral diol and an enantiomerically enriched non-racemic chiral epoxy compound by a hydrolytic kinetic resolution reaction.Type: GrantFiled: August 22, 2002Date of Patent: February 17, 2004Assignee: Rhodia Chirex, Inc.Inventors: Yi Liu, Marcello DiMare, Salvatore Anthony Marchese, Eric N. Jacobsen, Serge Jasmin
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Publication number: 20030073855Abstract: The present invention provides a process for the preparation of an enantiomerically enriched non-racemic chiral diol and an enantiomerically enriched non-racemic chiral epoxy compound by a hydrolytic kinetic resolution reaction. The process includes the step of contacting oxygen and mixture including a racemic chiral epoxy compound, a non-racemic Co(II) complex catalyst, an aromatic carboxylic acid and water, at a temperature and length of time sufficient to produce a mixture of said non-racemic chiral diol and said non-racemic chiral epoxy compound. The present invention also provides a process for the preparation of an enantiomerically enriched non-racemic chiral diol and an enantiomerically enriched non-racemic chiral epoxy compound by a hydrolytic kinetic resolution reaction.Type: ApplicationFiled: August 22, 2002Publication date: April 17, 2003Applicant: Rhodia ChiRex, Inc.Inventors: Yi Liu, Marcello DiMare, Salvatore Anthony Marchese, Eric N. Jacobsen, Serge Jasmin
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Patent number: 6489512Abstract: A method for making an indole compound includes transition metal-catalyzed arylation of a hydrazone to form an aryl hydrazone, hydrolysis of the aryl hydrazone to form an aryl hydrazine, and acid catalyzed cyclization of the aryl hydrazine to form the indole compound.Type: GrantFiled: June 21, 2002Date of Patent: December 3, 2002Assignee: Rhodia Chirex Inc.Inventors: Frederick Hicks, Da-Ming Gou, Salvatore Anthony Marchese, Lawrence J. Martel, Atena Necula, Richard E. Benetti, Richard A. Silva
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Patent number: 6448449Abstract: A process for the preparation of (R)-1-(2,3-difluoro-6-nitrophenoxy)-propan-2-ol, which is a useful intermediate in the synthesis of the widely used antibiotic Levofloxacin is provided. A process for the preparation of (R)-1-(2,3-difluoro-6-nitrophenoxy)-2-trimethylsiloxypropane is also described. The process includes the ring opening of (R)-propylene oxide with 2,3-difluoro-6-nitrophenyl trimethylsilyl ether in the presence of an optically active Co(salen) catalyst. The trimethylsilyl group of the reactant is transferred to the product aryloxy alcohol, which serves to protect the secondary alcohol in situ. Upon isolation, the trimethylsilyl group is removed and the resulting regioisomeric mixture purified to yield the desired (R)-1-(2,3-difluoro-6-nitrophenoxy)-propan-2-ol in high purity and yield.Type: GrantFiled: April 20, 2001Date of Patent: September 10, 2002Assignee: Rhodia ChiRex, Inc.Inventor: Jay Francis Larrow
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Publication number: 20020119909Abstract: The present invention includes a process for enantioselective preparation of a non-racemic compound, which is either usable as a fragrance or flavor component or is convertible to a fragrance or flavor component by one or more additional reaction steps. The process includes the step of contacting either a substrate capable of forming a non-racemic compound by an enantioselective reaction and a co-reactant in the presence of a non-racemic catalyst, or a non-racemic or enantiopure substrate and a co-reactant, optionally in the presence of a racemic or non-racemic catalyst. The contacting is carried out at a temperature and length of time that is sufficient to produce the non-racemic compound with high optical purity. The process is used in stereoselective preparation of enantiomerically enriched intermediates useful in the preparation of non-racemic, chiral flavor and fragrance components.Type: ApplicationFiled: January 17, 2002Publication date: August 29, 2002Applicant: Rhodia ChiRex, Inc.Inventors: Roger B. Pettman, Richard A. Silva, Jay Francis Larrow, Isabelle Storet
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Publication number: 20020007090Abstract: A process for the preparation of (R)-1-(2,3-difluoro-6-nitrophenoxy)-propan-2-ol, which is a useful intermediate in the synthesis of the widely used antibiotic Levofloxacin is provided. A process for the preparation of (R)-1-(2,3-difluoro-6-nitrophenoxy)-2-trimethylsiloxypropane is also described. The process includes the ring opening of (R)-propylene oxide with 2,3-difluoro-6-nitrophenyl trimethylsilyl ether in the presence of an optically active Co(salen) catalyst. The trimethylsilyl group of the reactant is transferred to the product aryloxy alcohol, which serves to protect the secondary alcohol in situ. Upon isolation, the trimethylsilyl group is removed and the resulting regioisomeric mixture purified to yield the desired (R)-1-(2,3-difluoro-6-nitrophenoxy)-propan-2-ol in high purity and yield.Type: ApplicationFiled: April 20, 2001Publication date: January 17, 2002Applicant: Rhodia Chirex, Inc.Inventor: Jay Francis Larrow