(6R,7S)-7-((R)-2-tert-Butoxycarbonylamino-2-phenyl-acetylamino)-3-methanesulfonyl-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Base Information

Chemical Name:(6R,7S)-7-((R)-2-tert-Butoxycarbonylamino-2-phenyl-acetylamino)-3-methanesulfonyl-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CAS No.:124494-93-5
Molecular Formula:C₂₂H₂₇N₃O₈S
Molecular Weight:493.538
Hs Code.:

Synonyms:(6R,7S)-7-((R)-2-tert-Butoxycarbonylamino-2-phenyl-acetylamino)-3-methanesulfonyl-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

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Chemical Property of (6R,7S)-7-((R)-2-tert-Butoxycarbonylamino-2-phenyl-acetylamino)-3-methanesulfonyl-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

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Technology Process of (6R,7S)-7-((R)-2-tert-Butoxycarbonylamino-2-phenyl-acetylamino)-3-methanesulfonyl-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

There total 7 articles about (6R,7S)-7-((R)-2-tert-Butoxycarbonylamino-2-phenyl-acetylamino)-3-methanesulfonyl-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 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: 73.0%

: 123151-27-9
allyl 7β-<amino>phenylacetyl>amino>-3-(methylsulfonyl)-1-carba-1-dethia-3-cephem-4-carboxylate

: 124494-93-5
(6R,7S)-7-((R)-2-tert-Butoxycarbonylamino-2-phenyl-acetylamino)-3-methanesulfonyl-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Guidance literature:: With tri-n-butyl-tin hydride; triphenylphosphine; palladium diacetate; In diethyl ether; acetonitrile; for 1h; Ambient temperature;
DOI:10.1021/jm00131a005

Reference yield:

: 123077-99-6
7β-[(phenoxyacetyl)amino]-3-{[(trifluoromethyl)sulfonyl]oxy}-1-carba-1-dethia-3-cephem-4-carboxylic acid

: 124494-93-5
(6R,7S)-7-((R)-2-tert-Butoxycarbonylamino-2-phenyl-acetylamino)-3-methanesulfonyl-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) NaHCO₃, tetra-n-butylammonium sulfate / 1.) H₂O, 2.) CH₃CN, room temperature, 2 d

3: 1.) chlorodimethoxytriazine, N-methylmorpholine / 1.) CH₂Cl₂, 0 deg C, 2 h, 2.) CH₂Cl₂, a) 0 deg C -> room temperature, b) room temperature, 2 d

4: 77 percent / dimethylformamide / 15 h / Ambient temperature

5: 73 percent / Ph₃P, n-Bu₃SnH / Pd(OAc)2 / acetonitrile; diethyl ether / 1 h / Ambient temperature

With 4-methyl-morpholine; chloro-dimethoxy-triazine; tri-n-butyl-tin hydride; sodium hydrogencarbonate; tetrabutylammonium sulfate; triphenylphosphine; palladium diacetate; In diethyl ether; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jm00131a005

Reference yield:

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

: 124494-93-5
(6R,7S)-7-((R)-2-tert-Butoxycarbonylamino-2-phenyl-acetylamino)-3-methanesulfonyl-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 15.07 g / Zn, 1 N HCl / dimethylformamide; tetrahydrofuran / 4 h / Ambient temperature

2: 1.) NaHCO₃, tetra-n-butylammonium sulfate / 1.) H₂O, 2.) CH₃CN, room temperature, 2 d

4: 1.) chlorodimethoxytriazine, N-methylmorpholine / 1.) CH₂Cl₂, 0 deg C, 2 h, 2.) CH₂Cl₂, a) 0 deg C -> room temperature, b) room temperature, 2 d

5: 77 percent / dimethylformamide / 15 h / Ambient temperature

6: 73 percent / Ph₃P, n-Bu₃SnH / Pd(OAc)2 / acetonitrile; diethyl ether / 1 h / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; chloro-dimethoxy-triazine; tri-n-butyl-tin hydride; sodium hydrogencarbonate; tetrabutylammonium sulfate; triphenylphosphine; zinc; palladium diacetate; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jm00131a005