(6R,7S)-8-Oxo-7-(2-phenoxy-acetylamino)-3-trifluoromethyl-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Base Information

Chemical Name:(6R,7S)-8-Oxo-7-(2-phenoxy-acetylamino)-3-trifluoromethyl-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester
CAS No.:142121-64-0
Molecular Formula:C₂₄H₂₀F₃N₃O₇
Molecular Weight:519.434
Hs Code.:

Synonyms:(6R,7S)-8-Oxo-7-(2-phenoxy-acetylamino)-3-trifluoromethyl-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester

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Chemical Property of (6R,7S)-8-Oxo-7-(2-phenoxy-acetylamino)-3-trifluoromethyl-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester

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Technology Process of (6R,7S)-8-Oxo-7-(2-phenoxy-acetylamino)-3-trifluoromethyl-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester

There total 2 articles about (6R,7S)-8-Oxo-7-(2-phenoxy-acetylamino)-3-trifluoromethyl-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl 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: 69.0%

: 75-61-6
dibromodifluoromethane

: 209680-82-0
(6R,7S)-3-Bromo-8-oxo-7-(2-phenoxy-acetylamino)-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester

: 142121-64-0
(6R,7S)-8-Oxo-7-(2-phenoxy-acetylamino)-3-trifluoromethyl-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: With copper(I) bromide; zinc; In N,N-dimethyl-formamide;
DOI:10.1016/S0960-894X(98)00204-2

Reference yield:

: 108493-71-6
p-nitrobenzyl (7S,6R)-7-(phenoxyacetamido)-3-{[(trifluoromethyl)sulfonyl]oxy}-1-carba-1-dethia-3-cephem-4-carboxylate

: 142121-64-0
(6R,7S)-8-Oxo-7-(2-phenoxy-acetylamino)-3-trifluoromethyl-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) LiBr, 2,6-lutidine, 2.) DBU / 1.) DMF, 2.) CH₂Cl₂

2: 69 percent / Zn, CuBr / dimethylformamide

With 2,6-dimethylpyridine; 1,8-diazabicyclo[5.4.0]undec-7-ene; copper(I) bromide; lithium bromide; zinc; In N,N-dimethyl-formamide;
DOI:10.1016/S0960-894X(98)00204-2

Reference yield:

: 142121-64-0
(6R,7S)-8-Oxo-7-(2-phenoxy-acetylamino)-3-trifluoromethyl-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester

: (6R,7S)-7-[(R)-2-Amino-2-(3-fluoro-phenyl)-acetylamino]-8-oxo-3-trifluoromethyl-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Guidance literature:: Multi-step reaction with 6 steps

1: Zn, HCl

2: Bu₄NHSO₄

3: 77 percent / PCl₅, i-BuOH

4: 1-chloro-3,5-dimethoxytriazine, NMM / CH₂Cl₂

5: Pd(PPh₃)4, n-Bu₃SnH

6: TFA, Et₃SiH

With 4-methyl-morpholine; hydrogenchloride; triethylsilane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2-methyl-propan-1-ol; 1-chloro-3,5-dimethoxytriazine; phosphorus pentachloride; tri-n-butyl-tin hydride; tetra(n-butyl)ammonium hydrogensulfate; trifluoroacetic acid; zinc; In dichloromethane;
DOI:10.1016/S0960-894X(98)00204-2