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

Base Information

Chemical Name:(1'R,5''S)-1-acetyl-6-bromo-3-{1'-azido-2'-oxo-2'-(2''-oxo-5''-phenyl-3'',1''-oxazolidinyl)ethyl}indole
CAS No.:936824-49-6
Molecular Formula:C₂₁H₁₆BrN₅O₄
Molecular Weight:482.293
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1'R,5''S)-1-acetyl-6-bromo-3-{1'-azido-2'-oxo-2'-(2''-oxo-5''-phenyl-3'',1''-oxazolidinyl)ethyl}indole

Chemical Property:

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Technology Process of (1'R,5''S)-1-acetyl-6-bromo-3-{1'-azido-2'-oxo-2'-(2''-oxo-5''-phenyl-3'',1''-oxazolidinyl)ethyl}indole

There total 1 articles about (1'R,5''S)-1-acetyl-6-bromo-3-{1'-azido-2'-oxo-2'-(2''-oxo-5''-phenyl-3'',1''-oxazolidinyl)ethyl}indole 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: 52.0%

: (5''S)-1-acetyl-6-bromo-2-methoxy-3-{2'-oxo-2'-(2''-oxo-5''-phenyl-3'',1''-oxazolidinyl)ethylidene}indoline

: 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

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

Guidance literature:: With methanesulfonic acid; trimethylsilylazide; 4 A molecular sieve; In dichloromethane; at 20 ℃; for 1h;
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

: C₂₁H₁₈N₃O₄Br

Guidance literature:: With hydrogenchloride; tributylphosphine; In tetrahydrofuran; at 0 - 20 ℃; for 12h;
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