42399-53-1

Basic information

• Product Name: (2RS,3RS)-cis-2,3-dihydro-5-[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one
• Synonyms: (2RS,3RS)-cis-2,3-dihydro-5-[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one
• CAS NO: 42399-53-1
• Molecular Weight: 372.488
• Mol File: 42399-53-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (2RS,3RS)-cis-2,3-dihydro-5-[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2RS,3RS)-cis-2,3-dihydro-5-[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one(42399-53-1)
• EPA Substance Registry System: (2RS,3RS)-cis-2,3-dihydro-5-[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one(42399-53-1)

Safety Data

• Hazardous Substances Data: 42399-53-1(Hazardous Substances Data)

Upstream product

• 27068-88-8 3c-hydroxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 107-99-3 2-(dimethylamino)ethyl chloride 
• 4584-46-7 (2-chloroethyl)dimethylamine hydrochloride 
• 42399-51-9 cis-(+)-2-(4'-methoxyphenyl)-3-hydroxy-2,3-dihydro-1,5-benzothiazepine-4(5H)-one 
• 27068-88-8 2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one 
• 30193-56-7 (+/-)-(R*,R*)-β-[(2-aminophenyl)thio]-α-hydroxy-4-methoxybenzenepropanoic acid, methyl ester 
• 123-11-5 4-methoxy-benzaldehyde 
• 96125-49-4 methyl trans-3-(4-methoxyphenyl)glycidate 
• 23515-44-8 5-(2-dimethylamino-ethyl)-3c-hydroxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 80344-17-8 3-[2-(2-dimethylamino-ethylamino)-phenylsulfanyl]-2-hydroxy-3-(4-methoxy-phenyl)-propionic acid 
• 154076-93-4 ethyl (Z)-2-(2-methoxyethoxy)methoxy-3-(4-methoxyphenyl)-2-propenoate 
• 137-07-5 2-amino-benzenethiol 
• 42245-42-1 methyl (2-RS,3-SR)-2,3-epoxy-3-(4-methoxyphenyl)propanoate 

Downstream Products

• 40602-19-5 3c-butyryloxy-5-(2-dimethylamino-ethyl)-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 40602-20-8 5-(2-dimethylamino-ethyl)-2r-(4-methoxy-phenyl)-3c-pentanoyloxy-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 
• 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 
• 42399-40-6 O-desacetyldiltiazem 
• 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 
• 68767-10-2 5-(2-dimethylamino-ethyl)-3c-hydroxy-2r-(4-methoxy-phenyl)-1,1-dioxo-1,2,3,5-tetrahydro-1λ⁶-benzo[b][1,4]thiazepin-4-one 
• 42399-54-2 (+)-Cis-3-(acetoxy)-5-[2-(dimethylamino)-ethyl]-2,3-dihydro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one hydrochloride 
• 129784-91-4 3c-benzoyloxy-5-(2-dimethylamino-ethyl)-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 68767-06-6 5-[2-(dimethyl-oxy-amino)-ethyl]-3c-hydroxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 68767-09-9 5-[2-(dimethyl-oxy-amino)-ethyl]-3c-hydroxy-2r-(4-methoxy-phenyl)-1,1-dioxo-1,2,3,5-tetrahydro-1λ⁶-benzo[b][1,4]thiazepin-4-one 
• 68767-08-8 5-[2-(dimethyl-oxy-amino)-ethyl]-3c-hydroxy-2r-(4-methoxy-phenyl)-1ξ-oxo-1,2,3,5-tetrahydro-1λ⁴-benzo[b][1,4]thiazepin-4-one 

Relevant articles and documents

Absolute conformation and configuration of (2S, 3S)-3-acetoxy-5-(dimethylaminoethyl)-2-(4-methoxyphenyl)-2,3-dihydro-1,5-ben zothiazepin-4(5H)-one chloride (dilthiazem hydrochloride)

-

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.

Stereoselective addition of 2-aminothiophenol to α-alkoxycinnamic acid derivatives - Alternative synthesis of (±)-diltiazem

A stereocontrolled synthesis of (±)-diltiazem by applying nucleophilic addition of 2-aminothiophenol to α-alkoxycinnamic acid derivatives is described.