(6R,7S)-8-Oxo-7-(2-phenoxy-acetylamino)-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

Base Information

Chemical Name:(6R,7S)-8-Oxo-7-(2-phenoxy-acetylamino)-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester
CAS No.:74560-19-3
Molecular Formula:C₂₂H₂₀N₂O₆
Molecular Weight:408.411
Hs Code.:

Synonyms:(6R,7S)-8-Oxo-7-(2-phenoxy-acetylamino)-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

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Chemical Property of (6R,7S)-8-Oxo-7-(2-phenoxy-acetylamino)-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

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Technology Process of (6R,7S)-8-Oxo-7-(2-phenoxy-acetylamino)-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

There total 9 articles about (6R,7S)-8-Oxo-7-(2-phenoxy-acetylamino)-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 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: 74.0%

: 74560-18-2
benzyl 2-triphenylphosphoranylidene-2-[2-oxo-3β-phenoxyacetamido-4β-(2-hydroxyethoxy)azetidin-1-yl]acetate

: 74560-19-3
(6R,7S)-8-Oxo-7-(2-phenoxy-acetylamino)-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

Guidance literature:: With pyridine; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In benzene; Ambient temperature;
DOI:10.1021/jm00184a009

Reference yield:

: 72217-21-1,72217-22-2
2-[(S)-3-Amino-2-(2-hydroxy-ethoxy)-4-oxo-azetidin-1-yl]-3-methyl-but-2-enoic acid benzyl ester

: 74560-19-3
(6R,7S)-8-Oxo-7-(2-phenoxy-acetylamino)-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: pyridine / 1.33 h / 0 °C

2: 1.) O₃, 2.) aq. NaHSO₃ / 1.) AcOEt, from -65 to 0 deg C, 2.) AcOEt

3: 9.46 g / Zn, AcOH / CH₂Cl₂ / 2 h / 5 °C

4: 2,6-lutidine, SOCl₂ / CH₂Cl₂ / 1 h / 0 °C

5: CH₂Cl₂ / 4 h / Heating

6: 1 N aq. NaOH / methanol / 0.25 h

7: 74 percent / pyridine, dicyclohexylcarbodiimide (DCC), DMSO, TFA / benzene / Ambient temperature

With pyridine; 2,6-dimethylpyridine; sodium hydroxide; thionyl chloride; ozone; sodium hydrogensulfite; acetic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; zinc; In methanol; dichloromethane; benzene;
DOI:10.1021/jm00184a009

Reference yield:

: 74560-15-9
benzyl 2-[2-oxo-3β-phenoxyacetamido-4β-(2-phenoxyacetoxyethoxy)azetidin-1-yl]glyoxylate

: 74560-19-3
(6R,7S)-8-Oxo-7-(2-phenoxy-acetylamino)-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 9.46 g / Zn, AcOH / CH₂Cl₂ / 2 h / 5 °C

2: 2,6-lutidine, SOCl₂ / CH₂Cl₂ / 1 h / 0 °C

3: CH₂Cl₂ / 4 h / Heating

4: 1 N aq. NaOH / methanol / 0.25 h

5: 74 percent / pyridine, dicyclohexylcarbodiimide (DCC), DMSO, TFA / benzene / Ambient temperature

With pyridine; 2,6-dimethylpyridine; sodium hydroxide; thionyl chloride; acetic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; zinc; In methanol; dichloromethane; benzene;
DOI:10.1021/jm00184a009