99109-07-6

Basic information

• Product Name: (αS,βS)-β-[(2-AMinophenyl)thio]-α-hydroxy-4-Methoxybenzenepropanoic Acid Methyl Ester
• Synonyms: (αS,βS)-β-[(2-AMinophenyl)thio]-α-hydroxy-4-Methoxybenzenepropanoic Acid Methyl Ester;[S-(R*,R*)]-β-[(2-AMinophenyl)thio]-α-hydroxy-4-Methoxybenzenepropanoic Acid Methyl Ester
• CAS NO: 99109-07-6
• Molecular Formula: C₁₇H₁₉NO₄S
• Molecular Weight: 333.40206
• Product Categories: Amines;Aromatics;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 99109-07-6.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (αS,βS)-β-[(2-AMinophenyl)thio]-α-hydroxy-4-Methoxybenzenepropanoic Acid Methyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: (αS,βS)-β-[(2-AMinophenyl)thio]-α-hydroxy-4-Methoxybenzenepropanoic Acid Methyl Ester(99109-07-6)
• EPA Substance Registry System: (αS,βS)-β-[(2-AMinophenyl)thio]-α-hydroxy-4-Methoxybenzenepropanoic Acid Methyl Ester(99109-07-6)

Safety Data

• Hazardous Substances Data: 99109-07-6(Hazardous Substances Data)

Usage

Uses

An impurity of Diltiazem (D460620).

Upstream product

• 4875-10-9 o-nitrothiophenol 
• 42245-42-1 methyl (2-RS,3-SR)-2,3-epoxy-3-(4-methoxyphenyl)propanoate 
• 137-07-5 2-amino-benzenethiol 
• 96125-49-4 methyl trans-3-(4-methoxyphenyl)glycidate 
• 123-11-5 4-methoxy-benzaldehyde 
• 30067-00-6 (2RS,3SR)-2-hydroxy-3-(4-methoxy-phenyl)-3-(2-nitro-phenylsulfanyl)-propionic acid methyl ester 
• 126060-70-6 (2R,3R)-3-(4-Methoxy-phenyl)-oxirane-2-carboxylic acid methyl ester 
• 127347-52-8 (2S,3R)-3-Hydroxy-3-(4-methoxy-phenyl)-2-(2,4,6-trichloro-benzenesulfonyloxy)-propionic acid methyl ester 
• 122517-80-0 (2S,3R)-(-)-methyl 2,3-dihydroxy-3-(p-methoxyphenyl)propionate 
• 105560-93-8 methyl (2R,3S)-3-(4-methoxyphenyl)glycidate 
• 125354-93-0 (2S,3S) methyl 2-hydroxy-3-(4-methoxyphenyl)-3-(2-nitrophenylthio)propionate 

Downstream Products

• 42399-49-5 (2S,3S)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one 
• 42399-41-7 diltiazem 
• 42399-53-1 (2RS,3RS)-cis-2,3-dihydro-5-[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one 
• 23515-44-8 5-(2-dimethylamino-ethyl)-3c-hydroxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 42399-40-6 O-desacetyldiltiazem 
• 27068-88-8 3c-hydroxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 42399-48-4 (2S,3S)-threo-2-hydroxy-3-(2-aminophenylthio)-3-(4-methoxyphenyl)-propionic acid 

Relevant articles and documents

Enantioselectivity of Pseudomonas cepacia lipase for the acetylation of 2-hydroxy carboxylic acid esters+

Structurally different ethyl or methyl 2-hydroxy carboxylates were resolved by Pseudomonas cepacia lipase-catalysed acetylations with vinyl acetate in diethylether. One type of the alcoholic substrates (2-hydroxy-2-arylacetates and 2-hydroxy-3-arylpropinates) contained a HO-group at the stereocentre. These compounds were resolved with high enantioselectivity (ee 91 → 99) at ca. 50% conversion. The other alcoholic substrates ((threo-2-hydroxy-3-methylbutyrate and threo- or erythro-2-hydroxy-3-aryl-3-arylthio(or aryloxy)propionates) with two stereocentres generally resulted in enantiopure products and the reactions stopped at 50 % conversion.

Process for preparing 1,5-benzothiazepine derivatives

There is disclosed a process for preparing 1,5-benzothiazepine derivatives of the formula: STR1 wherein R1 is a lower alkyl group, or a salt thereof which comprises subjecting a propionate derivatives of the formula: STR2 wherein R2 is an ester residue and R1 is the same as defined above, to intramolecular cyclization in the presence of a sulfonic acid compound of the formula: wherein R3 is a lower alkyl group or a substituted or unsubstituted phenyl group, in a non-halogenated organic solvent and, if desired, converting the product to a salt thereof.

Asymmetric syntheses of (+)-diltiazem hydrochloride

Efficient enantioselective syntheses of the important cardiac drug (+)-cis-(2S,3S)-diltiazem from (E)-methyl 4-methoxyphenylpropenoate via either the (2R,3S)- or (2S,3R)-enantiomers of threo-methyl 3-(4-methoxyphenyl)-2,3- dihydroxypropanoate are described.