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

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 2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one 
• 107-99-3 2-(dimethylamino)ethyl chloride 
• 27068-88-8 3c-hydroxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 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 
• 23515-44-8 5-(2-dimethylamino-ethyl)-3c-hydroxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-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 
• 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 
• 48218-47-9 5-(2-dimethylamino-ethyl)-3c-ethoxy-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 
• 40602-22-0 5-(2-dimethylamino-ethyl)-3c-hexanoyloxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 34933-06-7 (+/-)-Diltiazem 
• 33286-23-6 5-(2-dimethylamino-ethyl)-3c-hydroxy-2r-(4-hydroxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 68767-07-7 5-(2-dimethylamino-ethyl)-3c-hydroxy-2r-(4-methoxy-phenyl)-1ξ-oxo-1,2,3,5-tetrahydro-1λ⁴-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 
• 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 
• 68767-06-6 5-[2-(dimethyl-oxy-amino)-ethyl]-3c-hydroxy-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 129784-91-4 3c-benzoyloxy-5-(2-dimethylamino-ethyl)-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 42399-40-6 O-desacetyldiltiazem 
• 34933-06-7 3t-acetoxy-5-(2-dimethylamino-ethyl)-2r-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 

Relevant articles and documents

Process for preparing optically active 3-hydroxy-1,5-benzothiazepine derivative and intermediate therefor

An optical resolution process of the compound of the formula (1): STR1 wherein Ring A and Ring B are a substituted or unsubstituted benzene ring and R1 and R2 are the same or different and a lower alkyl group, by utilizing difference in solubility between the two diastereoisomeric salts prepared by treating the racemic compound (1) with an acidic resolution agent. The present process is industrially advantageous with compared to conventional processes for preparing an optically active 3-hydroxy-1,5-benzothiazepine derivative which are useful as an intermediate for preparing medicines.

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.

cis-(±)-5-[2- (Dimethylamino)ethyl]-3-hydroxy-2-(4- methoxyphenyl )-2,3,4,5-tetrahydro-1,5-benzothiazepin-4-one

The title compound, C20H24N2O3S, is a drug intermediate of diltiazem. The molecule is stabilized by covalent bonding and weak hydrogen bonding, and the crystal packing is stabilized by hydrogen bonding. The seven-membered ring is distorted showing a twist-boat conformation. The methoxyphenyl and hydroxy groups are cis oriented with respect to one another, with the phenyl ring in an axial position. Intermolecular hydrogen bonding produces dimers in the crystal.

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.