132830-16-1

Basic information

• Product Name: (-)-trans-(2S,3R)-2,3-dihydro-3-hydroxy-2-(4'-methoxyphenyl)-1,5-benzothiazepin-4-[5H]-one
• Synonyms: (-)-trans-(2S,3R)-2,3-dihydro-3-hydroxy-2-(4'-methoxyphenyl)-1,5-benzothiazepin-4-[5H]-one
• CAS NO: 132830-16-1
• Molecular Weight: 301.366
• Mol File: 132830-16-1.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: (-)-trans-(2S,3R)-2,3-dihydro-3-hydroxy-2-(4'-methoxyphenyl)-1,5-benzothiazepin-4-[5H]-one(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-trans-(2S,3R)-2,3-dihydro-3-hydroxy-2-(4'-methoxyphenyl)-1,5-benzothiazepin-4-[5H]-one(132830-16-1)
• EPA Substance Registry System: (-)-trans-(2S,3R)-2,3-dihydro-3-hydroxy-2-(4'-methoxyphenyl)-1,5-benzothiazepin-4-[5H]-one(132830-16-1)

Safety Data

• Hazardous Substances Data: 132830-16-1(Hazardous Substances Data)

Upstream product

• 30193-57-8 (+/-)-(R*,R*)-β-<(2-aminophenyl)thio>-α-hydroxy-4-methoxybenzenepropanoic acid 
• 96125-49-4 methyl trans-3-(4-methoxyphenyl)glycidate 
• 137-07-5 2-amino-benzenethiol 
• 42245-42-1 methyl (2-RS,3-SR)-2,3-epoxy-3-(4-methoxyphenyl)propanoate 
• 30193-56-7 (+/-)-(R*,R*)-β-[(2-aminophenyl)thio]-α-hydroxy-4-methoxybenzenepropanoic acid, methyl ester 
• 123-11-5 4-methoxy-benzaldehyde 
• 154076-93-4 ethyl (Z)-2-(2-methoxyethoxy)methoxy-3-(4-methoxyphenyl)-2-propenoate 
• 30067-00-6 (2RS,3SR)-2-hydroxy-3-(4-methoxy-phenyl)-3-(2-nitro-phenylsulfanyl)-propionic acid methyl ester 
• 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 
• 30193-56-7 (2RS,3RS)-3-(2'-aminophenylthio)-2-hydroxy-3-(4''-methoxyphenyl)-propionic acid methyl ester 
• 97801-79-1 2-(4-methoxyphenyl)-1,5-benzothiazepine-3,4(2H,5H)-dione 
• 131613-02-0 (2S,3R)-3-(2-Amino-phenylsulfanyl)-2-hydroxy-3-(4-methoxy-phenyl)-propionic acid 
• 27068-88-8 3c-hydroxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 

Downstream Products

• 81353-09-5 3c-hydroxy-2r-(4-methoxy-phenyl)-5-(2-methylamino-ethyl)-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 
• 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 
• 42399-53-1 (2RS,3RS)-cis-2,3-dihydro-5-[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one 
• 42399-49-5 (2S,3S)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one 
• 132830-17-2 trans-(2R,3S)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one 
• 97801-79-1 2-(4-methoxyphenyl)-1,5-benzothiazepine-3,4(2H,5H)-dione 
• 34933-06-7 (+/-)-Diltiazem 
• 128487-98-9 (RS)-2-(4-methoxyphenyl)-2-methyl-1,5-benzothiazepine-3,4(2H,5H)-dione 
• 128488-00-6 (RS)-2-allyl-2-(4-methoxyphenyl)-1,5-benzothiazepine-3,4-(2H,5H)-dione 
• 128487-99-0 2-Ethyl-2-(4-methoxy-phenyl)-5H-benzo[b][1,4]thiazepine-3,4-dione 
• 132814-93-8 (RS)-4-ethoxy-2-(4-methoxyphenyl)-2-methyl-1,5-benzothiazepin-3(2H)-one 
• 128487-90-1 4-ethoxy-3-methoxy-2-(4-methoxyphenyl)-1,5-benzothiazepine 

Relevant articles and documents

Facile ionic liquid-mediated protocol for the regioselective synthesis of 1,5-benzothiazepines

An efficient one-step ionic liquid-mediated green protocol for the regioselective synthesis of (+)=(±)-cis-2-(4-methoxy/benzyloxyphenyl)-3- hydroxy-2,3-dihydro-1,5- benzothiazepin-4-[5H]-ones has been developed from the reaction between substituted 2-aminobenzenethiol and methyl-(±)-trans-3- (4-methoxy/benzyloxy phenyl)glycidate, under nitrogen atmosphere, at 60±2 °C. The reaction has been performed in ionic liquids (viz, 1-butyl-3-methylimidazolium bromide/hexafluorophosphate), and the yields of the 1,5-benzothiazepine derivatives were found to be excellent. The cis-stereoisomer was obtained as the major product along with a trans-isomer as minor product.

Novel protocol for the asymmetric synthesis of 3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one via bakers' yeast reduction

A novel protocol for the asymmetric synthesis of 3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one is reported. Darzens condensation reactions of anisaldehyde with dichloroacetates, followed substitution reaction of sodium o-nitrophenylthiolate and bakers' yeast reduction furnished 2-hydroxy-3-(4-methoxyphenyl)-3-(2-nitrophenylsulfanyl)-propionates. Further reduction of a nitro group and cyclization gave the title compound.

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.