27068-88-8

Basic information

• Product Name: (2S,3S)-3-HYDROXY-2-(4-METHOXY-PHEN YL)-2,3-DIHYDRO-5H-BENZO[B][1,4]THI AZEPIN-4-ONE
• Synonyms: (2S,3S)-3-HYDROXY-2-(4-METHOXY-PHENYL)-2,3-DIHYDRO-5H-BENZO[B][1,4]THIAZEPIN-4-ONE
• CAS NO: 27068-88-8
• Molecular Formula: C₁₆H₁₅NO₃S
• Molecular Weight: 301.36
• Mol File: 27068-88-8.mol
• Article Data: 13

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2S,3S)-3-HYDROXY-2-(4-METHOXY-PHEN YL)-2,3-DIHYDRO-5H-BENZO[B][1,4]THI AZEPIN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S)-3-HYDROXY-2-(4-METHOXY-PHEN YL)-2,3-DIHYDRO-5H-BENZO[B][1,4]THI AZEPIN-4-ONE(27068-88-8)
• EPA Substance Registry System: (2S,3S)-3-HYDROXY-2-(4-METHOXY-PHEN YL)-2,3-DIHYDRO-5H-BENZO[B][1,4]THI AZEPIN-4-ONE(27068-88-8)

Safety Data

• Hazardous Substances Data: 27068-88-8(Hazardous Substances Data)

Usage

General Description

The chemical compound "(2S,3S)-3-HYDROXY-2-(4-METHOXY-PHEN YL)-2,3-DIHYDRO-5H-BENZO[B][1,4]THI AZEPIN-4-ONE" is a dihydrobenzothiazepinone derivative with a hydroxy group and a methoxyphenyl group. It has a molecular formula C16H15NO3S and a molecular weight of 309.36 g/mol. (2S,3S)-3-HYDROXY-2-(4-METHOXY-PHEN YL)-2,3-DIHYDRO-5H-BENZO[B][1,4]THI AZEPIN-4-ONE has potential pharmaceutical properties and may be used in medicinal chemistry for the development of new drugs for various therapeutic applications. Its specific pharmacological and biological activities are subject to further research and investigation.

Upstream product

• 137-07-5 2-amino-benzenethiol 
• 96125-49-4 methyl trans-3-(4-methoxyphenyl)glycidate 
• 30193-56-7 (2RS,3RS)-3-(2'-aminophenylthio)-2-hydroxy-3-(4''-methoxyphenyl)-propionic acid methyl ester 
• 42245-42-1 methyl (2-RS,3-SR)-2,3-epoxy-3-(4-methoxyphenyl)propanoate 
• 30193-57-8 erythro-(-)-3-((2-aminophenyl)thio)-2-hydroxy-3-(4-methoxyphenyl)propionic acid 
• 30193-57-8 erythro-(+)-3-((2-aminophenyl)thio)-2-hydroxy-3-(4-methoxyphenyl)propionic acid 
• 30067-00-6 (2RS,3SR)-2-hydroxy-3-(4-methoxy-phenyl)-3-(2-nitro-phenylsulfanyl)-propionic acid methyl ester 
• 154076-93-4 ethyl (Z)-2-(2-methoxyethoxy)methoxy-3-(4-methoxyphenyl)-2-propenoate 
• 123-11-5 4-methoxy-benzaldehyde 
• 30193-56-7 (+/-)-(R*,R*)-β-[(2-aminophenyl)thio]-α-hydroxy-4-methoxybenzenepropanoic acid, methyl ester 
• 30193-57-8 (+/-)-(R*,R*)-β-<(2-aminophenyl)thio>-α-hydroxy-4-methoxybenzenepropanoic acid 
• 6192-52-5 p-toluenesulfonic acid monohydrate 
• 42399-48-4 (2S,3S)-threo-2-hydroxy-3-(2-aminophenylthio)-3-(4-methoxyphenyl)-propionic acid 
• 16546-01-3 ethyl 3-(4-methoxyphenyl)-2,3-epoxypropionate 

Downstream Products

• 23515-44-8 5-(2-dimethylamino-ethyl)-3c-hydroxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 97801-78-0 3-acetoxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one 
• 129784-91-4 3c-benzoyloxy-5-(2-dimethylamino-ethyl)-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 40602-22-0 5-(2-dimethylamino-ethyl)-3c-hexanoyloxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 28739-41-5 5-(2-dimethylamino-ethyl)-3c-ethoxycarbonyloxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 48218-47-9 5-(2-dimethylamino-ethyl)-3c-ethoxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 31964-29-1 {2-[3c-acetoxy-2r-(4-methoxy-phenyl)-4-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazepin-5-yl]-ethyl}-ethyl-dimethyl-ammonium; bromide 
• 31964-30-4 {2-[3c-acetoxy-2r-(4-methoxy-phenyl)-4-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazepin-5-yl]-ethyl}-dimethyl-propyl-ammonium; bromide 
• 31964-28-0 {2-[3c-acetoxy-2r-(4-methoxy-phenyl)-4-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazepin-5-yl]-ethyl}-trimethyl-ammonium; iodide 
• 31964-31-5 {3-[3c-hydroxy-2r-(4-methoxy-phenyl)-4-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazepin-5-yl]-propyl}-trimethyl-ammonium; iodide 
• 31964-33-7 ethyl-dimethyl-{3-[3c-hydroxy-2r-(4-methoxy-phenyl)-4-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazepin-5-yl]-propyl}-ammonium; bromide 
• 31955-22-3 3c-benzyloxy-5-(2-dimethylamino-ethyl)-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 31953-21-6 3-methyl-butyric acid 5-(2-dimethylamino-ethyl)-2c-(4-methoxy-phenyl)-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3r-yl ester 
• 40602-20-8 5-(2-dimethylamino-ethyl)-2r-(4-methoxy-phenyl)-3c-pentanoyloxy-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 

Relevant articles and documents

Solid phase synthesis of hydroxy benzothiazepinones through cyclative release under thermolysis

Hydroxy benzothiazepinones were synthesized by a simple procedure involving epoxidation of polymer bound cinnamic acids followed by nucleophilic opening of the resulting glycidic ester by o-aminothiophenol to afford the intermediate hydroxy anilino-esters which underwent cyclization cleavage on heating in DMF to release the product completely.

Optical resolution of a 1,5-benzothiazepine derivative, a synthetic intermediate of diltiazem, by preferential crystallization and diastereomeric salt formation

Practical preparation methods of an optically active intermediate of diltiazem, (+)-(2S,3S)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-3-hydroxy-2- (4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one [(+)-7], have been developed by the use of physicochemical and chemical resolutions. 1) The salt of (+)-7 with 3-amino-4-hydroxy-benzenesulfonic acid (AHS), was found to exist as a conglomerate and could be reproducibly resolved into (+)-7·AHS and (-)- 7·AHS of 94-98% ee by a preferential crystallization procedure. 2) (+)- (1R)-3-Bromocamphor-9-sulfonic acid [(+)-BCS] was found to be an efficient resolving agent for (±)-7 and the diastereomeric resolution provided (+)- 7·(+)-BCS·2H2O salt in >43% yield and >97% ee by fractional crystallization. It is presumed that the crystal water of (+)-7·(+)- BCS·2H2O plays an important role in the selective crystallization during this efficient resolution.

A microwave synthesis of the cis and trans isomers of 3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one : The influence of solvent and power output on the diastereoselectivity

A diastereoselective one-pot synthesis and the trans- and cis-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H) -one nucleus, a key intermediate in the preparation of the calcium channel blocker Diltiazem, is carried out under microwave irradiation in an open vessel. Control of the diastereoselectivity is achieved by varying the reaction time and power output as well as the nature of the solvent.