1H-Indole-1-carboxylic acid, 5-bromo-3-[(1Z)-3-methoxy-3-oxo-2-[[(phenylmethoxy)carbonyl]amino]- 1-propenyl]-, 1,1-dimethylethyl ester

Base Information

• Chemical Name: 1H-Indole-1-carboxylic acid, 5-bromo-3-[(1Z)-3-methoxy-3-oxo-2-[[(phenylmethoxy)carbonyl]amino]- 1-propenyl]-, 1,1-dimethylethyl ester
• CAS No.: 395643-15-9
• Molecular Formula: C25H25BrN2O6
• Molecular Weight: 529.387
• Mol file: 395643-15-9.mol

Synonyms:

Chemical Property of 1H-Indole-1-carboxylic acid, 5-bromo-3-[(1Z)-3-methoxy-3-oxo-2-[[(phenylmethoxy)carbonyl]amino]- 1-propenyl]-, 1,1-dimethylethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1H-Indole-1-carboxylic acid, 5-bromo-3-[(1Z)-3-methoxy-3-oxo-2-[[(phenylmethoxy)carbonyl]amino]- 1-propenyl]-, 1,1-dimethylethyl ester

There total 2 articles about 1H-Indole-1-carboxylic acid, 5-bromo-3-[(1Z)-3-methoxy-3-oxo-2-[[(phenylmethoxy)carbonyl]amino]- 1-propenyl]-, 1,1-dimethylethyl 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: 91.0%

N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester (100945-15-1,88568-95-0) + 5-bromo-1-(tert-butoxycarbonyl)indole-3-carboxaldehyde (325800-39-3) → methyl (E)-2-(benzyloxycarbonyl)amino-3-[(1-tert-butoxycarbonyl-5-bromo)indol]aceylate + methyl (Z)-2-(benzyloxycarbonyl)amino-3-[(1-tert-butoxycarbonyl-5-bromo)indol]acrylate (395643-15-9)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 5h;

DOI:10.1016/S0040-4020(02)00162-X

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → methyl (Z)-2-(benzyloxycarbonyl)amino-3-[(1-tert-butoxycarbonyl-5-bromo)indol]acrylate (395643-15-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / CH₂Cl₂ / 4 h / 20 °C

2: 91 percent / DBU / CH₂Cl₂ / 5 h / 20 °C

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; 2: Horner-Emmons olefination;

DOI:10.1016/S0040-4020(02)00162-X

Reference yield: 100.0%

methyl (Z)-2-(benzyloxycarbonyl)amino-3-[(1-tert-butoxycarbonyl-5-bromo)indol]acrylate (395643-15-9) → (S)-5-bromo-1-tert-butoxycarbonyl-Nα-benzyloxycarbonyl-tryptophan methyl ester (395643-16-0)

Guidance literature:

With hydrogen; [(S,S)-Et-Du-PHOS)-Rh]OTf; In methanol; for 24h; under 3361.46 Torr;

DOI:10.1016/S0040-4020(02)00162-X

upstream raw materials:

N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester

5-bromo-1-(tert-butoxycarbonyl)indole-3-carboxaldehyde

di-tert-butyl dicarbonate

Downstream raw materials:

(S)-5-bromo-1-tert-butoxycarbonyl-N^α-benzyloxycarbonyl-tryptophan methyl ester

(R)-5-bromo-1-tert-butoxycarbonyl-N^α-benzyloxycarbonyl-tryptophan methyl ester