(S)-ethyl 3-[5-(2-benzyloxycarbonylamino-2-tert-butoxycarbonylethyl)-2-(4-methoxybenzyloxy)]phenyl-7-bromoindole-2-carboxylate

Base Information

Chemical Name:(S)-ethyl 3-[5-(2-benzyloxycarbonylamino-2-tert-butoxycarbonylethyl)-2-(4-methoxybenzyloxy)]phenyl-7-bromoindole-2-carboxylate
CAS No.:935846-54-1
Molecular Formula:C₄₀H₄₁BrN₂O₈
Molecular Weight:757.678
Hs Code.:

Synonyms:(S)-ethyl 3-[5-(2-benzyloxycarbonylamino-2-tert-butoxycarbonylethyl)-2-(4-methoxybenzyloxy)]phenyl-7-bromoindole-2-carboxylate

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Chemical Property of (S)-ethyl 3-[5-(2-benzyloxycarbonylamino-2-tert-butoxycarbonylethyl)-2-(4-methoxybenzyloxy)]phenyl-7-bromoindole-2-carboxylate

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Technology Process of (S)-ethyl 3-[5-(2-benzyloxycarbonylamino-2-tert-butoxycarbonylethyl)-2-(4-methoxybenzyloxy)]phenyl-7-bromoindole-2-carboxylate

There total 5 articles about (S)-ethyl 3-[5-(2-benzyloxycarbonylamino-2-tert-butoxycarbonylethyl)-2-(4-methoxybenzyloxy)]phenyl-7-bromoindole-2-carboxylate 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: 40.0%

: 935846-38-1
ethyl 7-bromo-3-iodoindole-2-carboxylate

: 935846-53-0
(S)-N-benzyloxycarbonyl-O-(4-methoxybenzyl)-3-[4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl]tyrosine tert-butyl ester

: 935846-54-1
(S)-ethyl 3-[5-(2-benzyloxycarbonylamino-2-tert-butoxycarbonylethyl)-2-(4-methoxybenzyloxy)]phenyl-7-bromoindole-2-carboxylate

Guidance literature:: With potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,2-dimethoxyethane; at 35 ℃; for 45h;
DOI:10.1021/jo062627r

Reference yield:

: 935846-57-4
(S)-N-benzyloxycarbonyl-O-(4-methoxybenzyl)-3-iodotyrosine tert-butyl ester

: 935846-54-1
(S)-ethyl 3-[5-(2-benzyloxycarbonylamino-2-tert-butoxycarbonylethyl)-2-(4-methoxybenzyloxy)]phenyl-7-bromoindole-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 70 percent / triethylamine; 2-(dicyclohexylphosphino)biphenyl / palladium(II) acetate / dioxane / 0.5 h / 85 °C

2: 40 percent / aq. potassium carbonate / PdCl₂(dppf)*CH₂Cl₂ / 1,2-dimethoxy-ethane / 45 h / 35 °C

With potassium carbonate; triethylamine; CyJohnPhos; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; palladium diacetate; In 1,4-dioxane; 1,2-dimethoxyethane;
DOI:10.1021/jo062627r

Reference yield:

: 16732-69-7
ethyl 7-bromo-1H-indole-2-carboxylate

: 935846-54-1
(S)-ethyl 3-[5-(2-benzyloxycarbonylamino-2-tert-butoxycarbonylethyl)-2-(4-methoxybenzyloxy)]phenyl-7-bromoindole-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: N-iodosuccinimide / dimethylformamide / 2 h / 20 °C

1.2: 83 percent / sodium thiosulfate / dimethylformamide; H₂O / 1 h

2.1: 40 percent / aq. potassium carbonate / PdCl₂(dppf)*CH₂Cl₂ / 1,2-dimethoxy-ethane / 45 h / 35 °C

With N-iodo-succinimide; potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,2-dimethoxyethane; N,N-dimethyl-formamide;
DOI:10.1021/jo062627r