ethyl 1-allyloxycarbonyl-3-[5-(2-benzyloxycarbonylamino-2-tert-butoxycarbonylethyl)-2-(4-methoxybenzyloxy)]phenyl-7-bromo-2-oxoindole-3-carboxylate

Base Information

Chemical Name:ethyl 1-allyloxycarbonyl-3-[5-(2-benzyloxycarbonylamino-2-tert-butoxycarbonylethyl)-2-(4-methoxybenzyloxy)]phenyl-7-bromo-2-oxoindole-3-carboxylate
CAS No.:935846-58-5
Molecular Formula:C₄₄H₄₅BrN₂O₁₁
Molecular Weight:857.752
Hs Code.:

ethyl 1-allyloxycarbonyl-3-[5-(2-benzyloxycarbonylamino-2-tert-butoxycarbonylethyl)-2-(4-methoxybenzyloxy)]phenyl-7-bromo-2-oxoindole-3-carboxylate

Synonyms:ethyl 1-allyloxycarbonyl-3-[5-(2-benzyloxycarbonylamino-2-tert-butoxycarbonylethyl)-2-(4-methoxybenzyloxy)]phenyl-7-bromo-2-oxoindole-3-carboxylate

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Chemical Property of ethyl 1-allyloxycarbonyl-3-[5-(2-benzyloxycarbonylamino-2-tert-butoxycarbonylethyl)-2-(4-methoxybenzyloxy)]phenyl-7-bromo-2-oxoindole-3-carboxylate

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Technology Process of ethyl 1-allyloxycarbonyl-3-[5-(2-benzyloxycarbonylamino-2-tert-butoxycarbonylethyl)-2-(4-methoxybenzyloxy)]phenyl-7-bromo-2-oxoindole-3-carboxylate

There total 8 articles about ethyl 1-allyloxycarbonyl-3-[5-(2-benzyloxycarbonylamino-2-tert-butoxycarbonylethyl)-2-(4-methoxybenzyloxy)]phenyl-7-bromo-2-oxoindole-3-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: 63.0%

: 935846-55-2
(S)-ethyl 3-[5-(2-benzyloxycarbonylamino-2-tert-butoxycarbonylethyl)-2-(4-methoxybenzyloxy)]phenyl-7-bromo-2-oxoindole-3-carboxylate

: 2937-50-0
Allyl chloroformate

: 935846-58-5
ethyl 1-allyloxycarbonyl-3-[5-(2-benzyloxycarbonylamino-2-tert-butoxycarbonylethyl)-2-(4-methoxybenzyloxy)]phenyl-7-bromo-2-oxoindole-3-carboxylate

Guidance literature:: (S)-ethyl 3-[5-(2-benzyloxycarbonylamino-2-tert-butoxycarbonylethyl)-2-(4-methoxybenzyloxy)]phenyl-7-bromo-2-oxoindole-3-carboxylate; Allyl chloroformate; With sodium hydride; In tetrahydrofuran; dichloromethane; at 0 - 20 ℃;

With dmap; In tetrahydrofuran; dichloromethane; for 2h; Further stages.;
DOI:10.1021/jo062627r

Reference yield:

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

: 935846-58-5
ethyl 1-allyloxycarbonyl-3-[5-(2-benzyloxycarbonylamino-2-tert-butoxycarbonylethyl)-2-(4-methoxybenzyloxy)]phenyl-7-bromo-2-oxoindole-3-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 40 percent / aq. potassium carbonate / PdCl₂(dppf)*CH₂Cl₂ / 1,2-dimethoxy-ethane / 45 h / 35 °C

2.1: tert-butyl hypochlorite / CH₂Cl₂ / 8 h / 20 °C

2.2: 68 percent / acetyl chloride / ethanol; CH₂Cl₂

3.1: sodium hydride / tetrahydrofuran; CH₂Cl₂; various solvent(s) / 0 - 20 °C

3.2: 63 percent / 4-(dimethylamino)pyridine / tetrahydrofuran; CH₂Cl₂; various solvent(s) / 2 h

With tert-butylhypochlorite; sodium hydride; potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane;
DOI:10.1021/jo062627r

Reference yield:

: 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

: 935846-58-5
ethyl 1-allyloxycarbonyl-3-[5-(2-benzyloxycarbonylamino-2-tert-butoxycarbonylethyl)-2-(4-methoxybenzyloxy)]phenyl-7-bromo-2-oxoindole-3-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 40 percent / aq. potassium carbonate / PdCl₂(dppf)*CH₂Cl₂ / 1,2-dimethoxy-ethane / 45 h / 35 °C

2.1: tert-butyl hypochlorite / CH₂Cl₂ / 8 h / 20 °C

2.2: 68 percent / acetyl chloride / ethanol; CH₂Cl₂

3.1: sodium hydride / tetrahydrofuran; CH₂Cl₂; various solvent(s) / 0 - 20 °C

3.2: 63 percent / 4-(dimethylamino)pyridine / tetrahydrofuran; CH₂Cl₂; various solvent(s) / 2 h

With tert-butylhypochlorite; sodium hydride; potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane;
DOI:10.1021/jo062627r