132830-17-2

Basic information

• Product Name: trans-(2R,3S)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one
• Synonyms: trans-(2R,3S)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one
• CAS NO: 132830-17-2
• Molecular Weight: 301.366
• Mol File: 132830-17-2.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: trans-(2R,3S)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: trans-(2R,3S)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one(132830-17-2)
• EPA Substance Registry System: trans-(2R,3S)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one(132830-17-2)

Safety Data

• Hazardous Substances Data: 132830-17-2(Hazardous Substances Data)

Upstream product

• 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 
• 97801-79-1 2-(4-methoxyphenyl)-1,5-benzothiazepine-3,4(2H,5H)-dione 
• 30067-00-6 (2RS,3SR)-2-hydroxy-3-(4-methoxy-phenyl)-3-(2-nitro-phenylsulfanyl)-propionic acid methyl ester 
• 30193-56-7 (2RS,3RS)-3-(2'-aminophenylthio)-2-hydroxy-3-(4''-methoxyphenyl)-propionic acid methyl ester 
• 27068-88-8 (+/-)-trans-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one 
• 97801-78-0 3-acetoxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one 
• 27068-88-8 3c-hydroxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 86603-46-5 3-(4-methoxy-phenyl)-3-(2-nitro-phenylsulfanyl)-2-oxo-propionic acid methyl ester 
• 131613-02-0 (2S,3R)-3-(2-Amino-phenylsulfanyl)-2-hydroxy-3-(4-methoxy-phenyl)-propionic acid 
• 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 

Downstream Products

• 42399-49-5 (2S,3S)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one 
• 97801-79-1 2-(4-methoxyphenyl)-1,5-benzothiazepine-3,4(2H,5H)-dione 
• 132830-16-1 (-)-trans-(2S,3R)-2,3-dihydro-3-hydroxy-2-(4'-methoxyphenyl)-1,5-benzothiazepin-4-[5H]-one 
• 91926-67-9 (2S,3R)-5-<2-(dimethylamino)ethyl>-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one 
• 111188-70-6 (2S,3R)-3-acetoxy-5-<2-(dimethylamino)ethyl>-2,3-dihydro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one 
• 91926-66-8 (2R,3S)-5-<2-(dimethylamino)ethyl>-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one 
• 111188-71-7 (2R,3S)-3-acetoxy-5-<2-(dimethylamino)ethyl>-2,3-dihydro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one 
• 34933-06-7 (+/-)-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 
• 42399-40-6 O-desacetyldiltiazem 
• 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 
• 81353-09-5 3c-hydroxy-2r-(4-methoxy-phenyl)-5-(2-methylamino-ethyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 128488-33-5 (2R,3R)-2-Benzyl-5-(2-dimethylamino-ethyl)-3-hydroxy-2-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 

Relevant articles and documents

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.

Asymmetric reduction of a 1,5-benzothiazepine derivative with sodium borohydride-(S)-α-amino acids: An efficient synthesis of a key intermediate of diltiazem

A key intermediate of diltiazem synthesis, (2S,3S)-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4 (5H)-one [(2S,3S)-1], has been efficiently synthesized by an asymmetric reduction of the prochiral ketone, 2-(4-methoxyphenyl)-1,5-benzothiazepine-3,4(2H,5H)-dione (3), with NaBH4 and chiral α-amino acids. As the chiral sources, β-branched-chain amino acids, such as (S)-valine, (S)-isoleucine, and (S)-tert-leucine, were found to be effective. In particular, using (S)-tert-leucine as a ligand resulted in the formation of (2S,3S)-1 with excellent enantioselectivity. (95% ee for cis-isomers). The addition of AcOH to the reaction permitted further improvement of both conversion and stereoselectivity. As a result, optically pure (2S,3S)-1 could be isolated in 86% yield. This asymmetric reduction proceeded via dynamic kinetic resolution and made it possible to control the two adjacent asymmetric carbons through keto-enol tautomerism.