(Z)-3-[4-Bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-2-tert-butoxycarbonylamino-acrylic acid methyl ester

Base Information

• Chemical Name: (Z)-3-[4-Bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-2-tert-butoxycarbonylamino-acrylic acid methyl ester
• CAS No.: 162893-61-0
• Molecular Formula: C₂₄H₂₅BrN₂O₆S
• Molecular Weight: 549.442
• Mol file: 162893-61-0.mol

Synonyms:(Z)-3-[4-Bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-2-tert-butoxycarbonylamino-acrylic acid methyl ester

Chemical Property of (Z)-3-[4-Bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-2-tert-butoxycarbonylamino-acrylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-3-[4-Bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-2-tert-butoxycarbonylamino-acrylic acid methyl ester

There total 3 articles about (Z)-3-[4-Bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-2-tert-butoxycarbonylamino-acrylic acid methyl ester 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: 87.0%

methyl 2-[(tert-butoxycarbonyl)amino]acrylate (55477-80-0) + 4-bromo-1-[(4-methylphenyl)sulfonyl]-1H-indole (90481-72-4) → (Z)-3-[4-Bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-2-tert-butoxycarbonylamino-acrylic acid methyl ester (162893-61-0)

Guidance literature:

With palladium diacetate; chloranil; sodium hydrogencarbonate; In 1,2-dichloro-ethane; at 83 ℃; for 8h;

DOI:10.1021/jo00111a004

Reference yield:

4-bromo-1H-indole (52488-36-5) → (Z)-3-[4-Bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-2-tert-butoxycarbonylamino-acrylic acid methyl ester (162893-61-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / NaH

2: 76 percent / Pd(OAc)2; NaHCO₃; p-chloranil

With palladium diacetate; chloranil; sodium hydride; sodium hydrogencarbonate;

DOI:10.1016/S0040-4039(01)00002-8

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → (Z)-3-[4-Bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-2-tert-butoxycarbonylamino-acrylic acid methyl ester (162893-61-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / NaH

2: 76 percent / Pd(OAc)2; NaHCO₃; p-chloranil

With palladium diacetate; chloranil; sodium hydride; sodium hydrogencarbonate;

DOI:10.1016/S0040-4039(01)00002-8

upstream raw materials:

methyl 2-[(tert-butoxycarbonyl)amino]acrylate

4-bromo-1-[(4-methylphenyl)sulfonyl]-1H-indole

4-bromo-1H-indole

p-toluenesulfonyl chloride

Downstream raw materials:

{1-[4-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-ylmethyl]-3-trimethylsilanyl-prop-2-ynyl}-methyl-carbamic acid tert-butyl ester

{1-[4-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-ylmethyl]-prop-2-ynyl}-methyl-carbamic acid tert-butyl ester

(S)-4-bromo-N-(tert-butoxycarbonyl)-1-tosyltryptophan methyl ester

N-(tert-butoxycarbonyl)-4-bromo-1-tosyl-D-tryptophan methyl ester