(R)-2-(6''-bromoindol-3''-yl)-{N-2'-(6'''-bromo-1'''-tosylindol-3'''-yl)-2'-(tert-butoxycarbonylamino)ethyl}-2-oxoethanamide

Base Information

Chemical Name:(R)-2-(6''-bromoindol-3''-yl)-{N-2'-(6'''-bromo-1'''-tosylindol-3'''-yl)-2'-(tert-butoxycarbonylamino)ethyl}-2-oxoethanamide
CAS No.:936824-56-5
Molecular Formula:C₃₂H₃₀Br₂N₄O₆S
Molecular Weight:758.487
Hs Code.:

Synonyms:(R)-2-(6''-bromoindol-3''-yl)-{N-2'-(6'''-bromo-1'''-tosylindol-3'''-yl)-2'-(tert-butoxycarbonylamino)ethyl}-2-oxoethanamide

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Chemical Property of (R)-2-(6''-bromoindol-3''-yl)-{N-2'-(6'''-bromo-1'''-tosylindol-3'''-yl)-2'-(tert-butoxycarbonylamino)ethyl}-2-oxoethanamide

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Technology Process of (R)-2-(6''-bromoindol-3''-yl)-{N-2'-(6'''-bromo-1'''-tosylindol-3'''-yl)-2'-(tert-butoxycarbonylamino)ethyl}-2-oxoethanamide

There total 9 articles about (R)-2-(6''-bromoindol-3''-yl)-{N-2'-(6'''-bromo-1'''-tosylindol-3'''-yl)-2'-(tert-butoxycarbonylamino)ethyl}-2-oxoethanamide 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: 72.0%

: 108061-76-3
2-(6-bromo-1H-indol-3-yl)-2-oxoacetyl chloride

: 354538-36-6
(1R)-N-(tert-butyloxycarbonyl)-1-(N-tosyl-6-bromoindol-3-yl)-2-azidoethylamine

: 936824-56-5
(R)-2-(6''-bromoindol-3''-yl)-{N-2'-(6'''-bromo-1'''-tosylindol-3'''-yl)-2'-(tert-butoxycarbonylamino)ethyl}-2-oxoethanamide

Guidance literature:: (1R)-N-(tert-butyloxycarbonyl)-1-(N-tosyl-6-bromoindol-3-yl)-2-azidoethylamine; With water; triphenylphosphine; In tetrahydrofuran; for 1h; Heating;

2-(6-bromo-1H-indol-3-yl)-2-oxoacetyl chloride; With triethylamine; In tetrahydrofuran; at 20 ℃; for 1h; Further stages.;
DOI:10.1055/s-2007-965907

Reference yield:

: 936824-55-4
tert-butyl (1R',5S'')-{1-(1'-acetyl-6'-bromoindol-3'-yl)-2-oxo-2-(2''-oxo-5''-phenyl-3'',1''-oxazolidinyl)}ethylcarbamate

: 936824-56-5
(R)-2-(6''-bromoindol-3''-yl)-{N-2'-(6'''-bromo-1'''-tosylindol-3'''-yl)-2'-(tert-butoxycarbonylamino)ethyl}-2-oxoethanamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaBH₄ / tetrahydrofuran; H₂O / 0.5 h / 20 °C

2.1: 0.68 g / aq. LiOH / tetrahydrofuran / 0.5 h / 20 °C

3.1: 92 percent / DMAP; Et₃N / CH₂Cl₂ / 20 h / -20 °C

4.1: 79 percent / NaN₃ / dimethylformamide / 1 h / 80 °C

5.1: Ph₃P; H₂O / tetrahydrofuran / 1 h / Heating

5.2: 72 percent / Et₃N / tetrahydrofuran / 1 h / 20 °C

With dmap; lithium hydroxide; sodium tetrahydroborate; sodium azide; water; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1055/s-2007-965907

Reference yield:

: 936824-49-6
(1'R,5''S)-1-acetyl-6-bromo-3-{1'-azido-2'-oxo-2'-(2''-oxo-5''-phenyl-3'',1''-oxazolidinyl)ethyl}indole

: 936824-56-5
(R)-2-(6''-bromoindol-3''-yl)-{N-2'-(6'''-bromo-1'''-tosylindol-3'''-yl)-2'-(tert-butoxycarbonylamino)ethyl}-2-oxoethanamide

Guidance literature:: Multi-step reaction with 7 steps

1.1: aq. HCl; n-Bu₃P / tetrahydrofuran / 12 h / 0 - 20 °C

2.1: 1.3 g / DMAP / CH₂Cl₂ / 72 h / 20 °C

3.1: NaBH₄ / tetrahydrofuran; H₂O / 0.5 h / 20 °C

4.1: 0.68 g / aq. LiOH / tetrahydrofuran / 0.5 h / 20 °C

5.1: 92 percent / DMAP; Et₃N / CH₂Cl₂ / 20 h / -20 °C

6.1: 79 percent / NaN₃ / dimethylformamide / 1 h / 80 °C

7.1: Ph₃P; H₂O / tetrahydrofuran / 1 h / Heating

7.2: 72 percent / Et₃N / tetrahydrofuran / 1 h / 20 °C

With hydrogenchloride; dmap; lithium hydroxide; sodium tetrahydroborate; sodium azide; tributylphosphine; water; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1055/s-2007-965907