42399-49-5

Basic information

• Product Name: (2S-cis)-(+)-2,3-Dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one
• Synonyms: HYDROXY LACTAM;(2S-CIS)-(+)-2,3-DIHYDRO-3-HYDROXY-2-(4-METHOXYPHENYL)-1,5-BENZOTHIAZEPIN-4(5H)-ONE;(2S-cis)-(+)-2,3-Dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one ,99%;DiltiazeM IMpurity E;3-hydroxy-2,3-dihydrobenzo[b][1,4]thiazepin-4(5H)-one;(2S,3S)-3-Hydroxy-2-(4-methoxyphenyl)-2,3-dihydrobenzo[b][1,4]thiazepin-4(5H)-one;(2S,3S)-(+)-2,3-Dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one;5-benzothiazepin-4(5h)-one,2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-(2s-c
• CAS NO: 42399-49-5
• Molecular Formula: C₁₆H₁₅NO₃S
• Molecular Weight: 301.36
• EINECS: 255-799-0
• Product Categories: Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds;Pharmaceutical Intermediates;Heterocycles series;INTERMEDIATESOFDILTIAZEM;API intermediates;Chiral Building Blocks;Heterocyclic Building Blocks;Others
• Mol File: 42399-49-5.mol
• Article Data: 40

Chemical Properties

• Melting Point: 203-206 °C(lit.)
• Boiling Point: 545.4 °C at 760 mmHg
• Flash Point: 283.7 °C
• Appearance: white to slightly beige powder
• Density: 1.2458 (rough estimate)
• Vapor Pressure: 9.95E-13mmHg at 25°C
• Refractive Index: 114 ° (C=0.5, MeOH)
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly, Sonicated)
• PKA: 12.37±0.40(Predicted)
• CAS DataBase Reference: (2S-cis)-(+)-2,3-Dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2S-cis)-(+)-2,3-Dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one(42399-49-5)
• EPA Substance Registry System: (2S-cis)-(+)-2,3-Dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one(42399-49-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 42399-49-5(Hazardous Substances Data)

Usage

Chemical Properties

white to slightly beige powder

Uses

A key intermediate for Diltiazem (D460620) synthesis.

InChI:InChI=1/C16H15NO3S/c1-20-11-8-6-10(7-9-11)15-14(18)16(19)17-12-4-2-3-5-13(12)21-15/h2-9,14-15,18H,1H3,(H,17,19)/t14-,15+/m1/s1

Upstream product

• 30193-56-7 (+/-)-(R*,R*)-β-[(2-aminophenyl)thio]-α-hydroxy-4-methoxybenzenepropanoic acid, methyl ester 
• 139893-86-0 Ethyl 2(S)-hydroxy-3(S)-<(O-aminophenyl)thio>-3-(p-methoxyphenyl)propionate 
• 24393-56-4 ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate 
• 195616-20-7 (2S,3S)-3-(2-aminophenylthio)-2-hydroxy-3-(4-methoxyphenyl)propionamide 
• 105560-93-8 methyl (2R,3S)-3-(4-methoxyphenyl)glycidate 
• 137-07-5 2-amino-benzenethiol 
• 30193-56-7 (2RS,3RS)-3-(2'-aminophenylthio)-2-hydroxy-3-(4''-methoxyphenyl)-propionic acid methyl ester 
• 20859-02-3 L-tert-Leucine 
• 97801-79-1 2-(4-methoxyphenyl)-1,5-benzothiazepine-3,4(2H,5H)-dione 
• 73-32-5 L-isoleucine 
• 97801-78-0 3-acetoxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one 
• 95-50-1 1,2-dichloro-benzene 
• 123-91-1 1,4-dioxane 
• 195616-19-4 (2R,3S)-3-(4-methoxyphenyl)glycidic amide 

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 
• 97859-66-0 Acetic acid (2S,3S)-5-acetyl-2-(4-methoxy-phenyl)-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3-yl ester 
• 33286-22-5 diltiazem hydrochloride 
• 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 
• 132830-16-1 (-)-trans-(2S,3R)-2,3-dihydro-3-hydroxy-2-(4'-methoxyphenyl)-1,5-benzothiazepin-4-[5H]-one 
• 128510-02-1 [2S-(2α,3α)]-2,3-Dihydro-5-[(4,5-dihydro-1H-imidazol-2-yl)methyl]-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one, monohydrochloride 
• 137447-97-3 (2S,3S)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydrobenzo[b][1,4]thiazepin-4(5H)-one 1-oxide 
• 87447-47-0 (2S,3S)-cis-3-acetoxy-2,3-dihydro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one 
• 97801-78-0 3-acetoxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one 
• 42399-40-6 O-desacetyldiltiazem 
• 1376615-78-9 5-(2-(dimethylamino)ethyl)-2-(4-methoxyphenyl)-2H-spiro[benzo[b][1,4]thiazepine-3,2'-[1,3]dioxolan]-4(5H)-one 
• 1376615-76-7 2-(4-methoxyphenyl)-2H-spiro[benzo[b][1,4]thiazepine-3,2'-[1,3]dioxolan]-4(5H)-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

Preparation method of 2-(4-methoxyphenyl)-3-hydroxy-2, 3-dihydro-1, 5-benzothiazepine ketone

The invention provides a preparation method of 2-(4-methoxyphenyl)-3-hydroxy-2, 3-dihydro-1, 5-benzothiazepine ketone. The preparation method comprises the following steps: taking o-aminothiophenol and methyl propiolate as raw materials to synthesize an intermediate product 1, carrying out selective epoxidation to obtain an intermediate product 2, reacting the intermediate product 2 with 4-methoxyphenyl anions, carrying out Mitsunobu reaction to obtain an intermediate product 3, and hydrolyzing to obtain the product. In the cyclization process of the intermediate product 1, the tension of Z-structure olefin is small so that the yield is high, subsequent epoxidation is an asymmetric epoxidation reaction, the obtained intermediate product 2 is high in optical purity and high in yield, the intermediate product 2 and 4-methoxyphenyl anions are subjected to SN2 reaction, configuration inversion is carried out in an ortho-position, and the product is obtained. The whole reaction process doesnot need to be split, the total yield of the route is high, and the method is economical.

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.