methyl (S)-4,5,6,7-tetrafluoro-3-(4-methoxyphenyl)-2,3-dihydrobenzo[d]isothiazole-3-carboxylate 1,1-dioxide

Base Information

• Chemical Name: methyl (S)-4,5,6,7-tetrafluoro-3-(4-methoxyphenyl)-2,3-dihydrobenzo[d]isothiazole-3-carboxylate 1,1-dioxide
• CAS No.: 1446282-84-3
• Molecular Formula: C₁₆H₁₁F₄NO₅S
• Molecular Weight: 405.327
• Mol file: 1446282-84-3.mol

Synonyms:methyl (S)-4,5,6,7-tetrafluoro-3-(4-methoxyphenyl)-2,3-dihydrobenzo[d]isothiazole-3-carboxylate 1,1-dioxide

Chemical Property of methyl (S)-4,5,6,7-tetrafluoro-3-(4-methoxyphenyl)-2,3-dihydrobenzo[d]isothiazole-3-carboxylate 1,1-dioxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (S)-4,5,6,7-tetrafluoro-3-(4-methoxyphenyl)-2,3-dihydrobenzo[d]isothiazole-3-carboxylate 1,1-dioxide

There total 4 articles about methyl (S)-4,5,6,7-tetrafluoro-3-(4-methoxyphenyl)-2,3-dihydrobenzo[d]isothiazole-3-carboxylate 1,1-dioxide 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:

methyl (S)-2-(4-methoxyphenyl)-2-(2,3,4,5,6-pentafluorophenylsulfonamido)acetate (1446282-69-4) → methyl (R)-4,5,6,7-tetrafluoro-3-(4-methoxyphenyl)-2,3-dihydrobenzo[d]isothiazole-3-carboxylate 1,1-dioxide (1446282-83-2) + methyl (S)-4,5,6,7-tetrafluoro-3-(4-methoxyphenyl)-2,3-dihydrobenzo[d]isothiazole-3-carboxylate 1,1-dioxide (1446282-84-3)

Guidance literature:

With N,N,N′,N′-tetramethyl-N″-tert-butylguanidine; 1,8-diazabicyclo[5.4.0]undec-7-ene; In 1,2-dimethoxyethane; at 0 - 25 ℃; for 96h; Overall yield = 99 %; Overall yield = 401 mg; enantioselective reaction;

DOI:10.1021/ol401557v

Reference yield:

(S)-tert-butoxycarbonylamino(4-methoxyphenyl)acetic acid methyl ester (183671-61-6) → methyl (R)-4,5,6,7-tetrafluoro-3-(4-methoxyphenyl)-2,3-dihydrobenzo[d]isothiazole-3-carboxylate 1,1-dioxide (1446282-83-2) + methyl (S)-4,5,6,7-tetrafluoro-3-(4-methoxyphenyl)-2,3-dihydrobenzo[d]isothiazole-3-carboxylate 1,1-dioxide (1446282-84-3)

Guidance literature:

Multi-step reaction with 3 steps

1: chloroform / 4 h / 0 - 20 °C

2: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 0 - 25 °C

3: N,N,N′,N′-tetramethyl-N″-tert-butylguanidine / 1,2-dimethoxyethane / 0 - 25 °C

With N,N,N′,N′-tetramethyl-N″-tert-butylguanidine; N-ethyl-N,N-diisopropylamine; In 1,2-dimethoxyethane; dichloromethane; chloroform;

DOI:10.1021/ol401557v

Reference yield:

N-tert-butyloxycarbonyl-L-4-hydroxyphenylglycine (69651-48-5) → methyl (R)-4,5,6,7-tetrafluoro-3-(4-methoxyphenyl)-2,3-dihydrobenzo[d]isothiazole-3-carboxylate 1,1-dioxide (1446282-83-2) + methyl (S)-4,5,6,7-tetrafluoro-3-(4-methoxyphenyl)-2,3-dihydrobenzo[d]isothiazole-3-carboxylate 1,1-dioxide (1446282-84-3)

Guidance literature:

Multi-step reaction with 4 steps

1: aluminum (III) chloride / methanol; diethyl ether / 4 h / 0 - 20 °C

2: chloroform / 4 h / 0 - 20 °C

3: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 0 - 25 °C

4: N,N,N′,N′-tetramethyl-N″-tert-butylguanidine / 1,2-dimethoxyethane / 0 - 25 °C

With aluminum (III) chloride; N,N,N′,N′-tetramethyl-N″-tert-butylguanidine; N-ethyl-N,N-diisopropylamine; In methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; chloroform;

DOI:10.1021/ol401557v

upstream raw materials:

N-tert-butyloxycarbonyl-L-4-hydroxyphenylglycine

methyl (S)-2-(4-methoxyphenyl)-2-(2,3,4,5,6-pentafluorophenylsulfonamido)acetate

(S)-tert-butoxycarbonylamino(4-methoxyphenyl)acetic acid methyl ester

(S)-2-amino-2-(4-methoxy-phenyl)acetic acid methyl ester