methyl α-(4R-acetylthio-3S-methoxy-3-phenoxyacetamido-2-azetidinon-1-yl)-β-methylcrotonate

Base Information

Chemical Name:methyl α-(4R-acetylthio-3S-methoxy-3-phenoxyacetamido-2-azetidinon-1-yl)-β-methylcrotonate
CAS No.:84161-62-6
Molecular Formula:C₂₀H₂₄N₂O₇S
Molecular Weight:436.486
Hs Code.:

Synonyms:methyl α-(4R-acetylthio-3S-methoxy-3-phenoxyacetamido-2-azetidinon-1-yl)-β-methylcrotonate

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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 methyl α-(4R-acetylthio-3S-methoxy-3-phenoxyacetamido-2-azetidinon-1-yl)-β-methylcrotonate

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Technology Process of methyl α-(4R-acetylthio-3S-methoxy-3-phenoxyacetamido-2-azetidinon-1-yl)-β-methylcrotonate

There total 5 articles about methyl α-(4R-acetylthio-3S-methoxy-3-phenoxyacetamido-2-azetidinon-1-yl)-β-methylcrotonate 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:

: 24652-74-2
methyl 6-phenoxyacetamidopenicillanate-1β-oxide

: 84161-62-6
methyl α-(4R-acetylthio-3S-methoxy-3-phenoxyacetamido-2-azetidinon-1-yl)-β-methylcrotonate

Guidance literature:: Multi-step reaction with 2 steps

1: 1) tBuOCl / 1) THF, MeOH, -75 deg C, 2) THF, MeOH, 15 min, -70 deg C, than 20 min, -50 deg C

2: 1) triethyl phosphite, 2) Et₃N / 1) toluene, 4 h, 2) ethyl acetate

With tert-butylhypochlorite; triethylamine; triethyl phosphite;
DOI:10.1039/c39820000933

Reference yield:

: 108-24-7
acetic anhydride

: 41625-69-8
methyl 6α-methoxy-6β-phenoxyacetamidopenicillanate-1β-oxide

: 84161-62-6
methyl α-(4R-acetylthio-3S-methoxy-3-phenoxyacetamido-2-azetidinon-1-yl)-β-methylcrotonate

Guidance literature:: With triethylamine; phosphorous acid trimethyl ester; Yield given. Multistep reaction; 1.)toluene, 96 deg C, 24 h 2.)ethyl acetate, 3 h;
DOI:10.1139/v88-225

Reference yield:

: 2-[(2R,3S)-2-tert-Butoxysulfinyl-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-3-methyl-but-2-enoic acid methyl ester

: 84161-62-6
methyl α-(4R-acetylthio-3S-methoxy-3-phenoxyacetamido-2-azetidinon-1-yl)-β-methylcrotonate

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) t-butyl hypochlorite / 1.) tetrahydrofuran - methanol, -78 deg C

With tert-butylhypochlorite;
DOI:10.1016/S0040-4039(00)81966-8