(+/-)-cis-9-fluoro-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one

Base Information

• Chemical Name: (+/-)-cis-9-fluoro-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one
• CAS No.: 100493-29-6
• Molecular Formula: C₁₆H₁₄FNO₃S
• Molecular Weight: 319.356
• Mol file: 100493-29-6.mol

Synonyms:(+/-)-cis-9-fluoro-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one

Chemical Property of (+/-)-cis-9-fluoro-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-cis-9-fluoro-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one

There total 5 articles about (+/-)-cis-9-fluoro-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.7%

(2S,3S)-3-(2-Amino-6-fluoro-phenylsulfanyl)-2-hydroxy-3-(4-methoxy-phenyl)-propionic acid methyl ester (100493-33-2) → (+/-)-cis-9-fluoro-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one (100493-29-6)

Guidance literature:

With sodium hydride; dimethyl sulfoxide; for 0.0833333h; Ambient temperature;

DOI:10.1021/jm00106a032

Reference yield: 4.5%

methyl trans-3-(4-methoxyphenyl)glycidate (96125-49-4) + 2-amino-6-fluorobenzenethiol (100493-32-1) → (2S,3S)-3-(2-Amino-6-fluoro-phenylsulfanyl)-2-hydroxy-3-(4-methoxy-phenyl)-propionic acid methyl ester (100493-33-2) + (+/-)-trans-(2R,3S)-9-fluoro-2,3-dihydro-3-hydroxy-2-(4'-methoxyphenyl)-1,5-benzothiazepin-4-[5H]-one (100601-58-9) + (+/-)-cis-9-fluoro-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one (100493-29-6)

Guidance literature:

at 160 ℃; for 16h;

DOI:10.1021/jm00106a032

Reference yield:

meta-fluoroaniline (372-19-0) → (+/-)-cis-9-fluoro-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one (100493-29-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 72 percent / bromine

2: 93.4 percent / aq. NaOH / Heating

3: 14.9 percent / 16 h / 160 °C

4: 87.7 percent / NaH, DMSO / 0.08 h / Ambient temperature

With sodium hydroxide; bromine; sodium hydride; dimethyl sulfoxide;

DOI:10.1021/jm00106a032

upstream raw materials:

methyl trans-3-(4-methoxyphenyl)glycidate

2-amino-6-fluorobenzenethiol

(2S,3S)-3-(2-Amino-6-fluoro-phenylsulfanyl)-2-hydroxy-3-(4-methoxy-phenyl)-propionic acid methyl ester

meta-fluoroaniline

Downstream raw materials:

Acetic acid (2R,3R)-5-(2-dimethylamino-ethyl)-9-fluoro-2-(4-methoxy-phenyl)-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3-yl ester

(2R,3R)-5-(2-Dimethylamino-ethyl)-9-fluoro-3-hydroxy-2-(4-methoxy-phenyl)-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one