Chloro-{(3R,4R)-2-oxo-3-(2-phenoxy-acetylamino)-4-[2-(2,2,2-trichloro-ethoxycarbonyloxy)-acetylsulfanyl]-azetidin-1-yl}-acetic acid benzyl ester

Base Information

Chemical Name:Chloro-{(3R,4R)-2-oxo-3-(2-phenoxy-acetylamino)-4-[2-(2,2,2-trichloro-ethoxycarbonyloxy)-acetylsulfanyl]-azetidin-1-yl}-acetic acid benzyl ester
CAS No.:73885-12-8
Molecular Formula:C₂₅H₂₂Cl₄N₂O₉S
Molecular Weight:668.336
Hs Code.:

Chloro-{(3R,4R)-2-oxo-3-(2-phenoxy-acetylamino)-4-[2-(2,2,2-trichloro-ethoxycarbonyloxy)-acetylsulfanyl]-azetidin-1-yl}-acetic acid benzyl ester

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Chemical Property of Chloro-{(3R,4R)-2-oxo-3-(2-phenoxy-acetylamino)-4-[2-(2,2,2-trichloro-ethoxycarbonyloxy)-acetylsulfanyl]-azetidin-1-yl}-acetic acid benzyl ester

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Technology Process of Chloro-{(3R,4R)-2-oxo-3-(2-phenoxy-acetylamino)-4-[2-(2,2,2-trichloro-ethoxycarbonyloxy)-acetylsulfanyl]-azetidin-1-yl}-acetic acid benzyl ester

There total 7 articles about Chloro-{(3R,4R)-2-oxo-3-(2-phenoxy-acetylamino)-4-[2-(2,2,2-trichloro-ethoxycarbonyloxy)-acetylsulfanyl]-azetidin-1-yl}-acetic 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:

: 73884-79-4
<<(Trichloroethoxy)carbonyl>oxy>acetyl Chloride

: 73885-12-8,74643-18-8,74643-19-9
Chloro-{(3R,4R)-2-oxo-3-(2-phenoxy-acetylamino)-4-[2-(2,2,2-trichloro-ethoxycarbonyloxy)-acetylsulfanyl]-azetidin-1-yl}-acetic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 7.00 g / pyridine / CH₂Cl₂ / 0.25 h / -15 °C

2: 30 percent / Et₃N / benzene / 1.17 h / Ambient temperature

3: 87 percent / O₃ / ethyl acetate / -78 °C

4: 1.88 g / 1.) Al-Hg; 2.) AcOH, H₂O / 5 °C / 1.) THF; 2.) 70 min

5: 1.) 2,6-lutidine; 2.) SOCl₂ / CH₂Cl₂ / 1.) -40 deg C; 2.) -40 -> -5 deg C, 30 min

With pyridine; 2,6-dimethylpyridine; thionyl chloride; aluminium amalgam; water; ozone; acetic acid; triethylamine; In dichloromethane; ethyl acetate; benzene;
DOI:10.1016/S0040-4020(01)97686-0

Reference yield:

: 68047-65-4
(R)-2-[(2R)-2r-mercapto-4-oxo-3c-(2-phenoxy-acetylamino)-azetidin-1-yl]-3-methyl-but-3-enoic acid benzyl ester

: 73885-12-8,74643-18-8,74643-19-9
Chloro-{(3R,4R)-2-oxo-3-(2-phenoxy-acetylamino)-4-[2-(2,2,2-trichloro-ethoxycarbonyloxy)-acetylsulfanyl]-azetidin-1-yl}-acetic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 7.00 g / pyridine / CH₂Cl₂ / 0.25 h / -15 °C

2: 30 percent / Et₃N / benzene / 1.17 h / Ambient temperature

3: 87 percent / O₃ / ethyl acetate / -78 °C

4: 1.88 g / 1.) Al-Hg; 2.) AcOH, H₂O / 5 °C / 1.) THF; 2.) 70 min

5: 1.) 2,6-lutidine; 2.) SOCl₂ / CH₂Cl₂ / 1.) -40 deg C; 2.) -40 -> -5 deg C, 30 min

With pyridine; 2,6-dimethylpyridine; thionyl chloride; aluminium amalgam; water; ozone; acetic acid; triethylamine; In dichloromethane; ethyl acetate; benzene;
DOI:10.1016/S0040-4020(01)97686-0

Reference yield:

: 78549-42-5
benzyl (2R)-2-<(3R,4R)-3-phenoxyacetamido-4-trichloroethoxycarbonyloxyacetylthio-2-oxoazetidin-1-yl>-3-methylbut-3-enoate

: 73885-12-8,74643-18-8,74643-19-9
Chloro-{(3R,4R)-2-oxo-3-(2-phenoxy-acetylamino)-4-[2-(2,2,2-trichloro-ethoxycarbonyloxy)-acetylsulfanyl]-azetidin-1-yl}-acetic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 30 percent / Et₃N / benzene / 1.17 h / Ambient temperature

2: 87 percent / O₃ / ethyl acetate / -78 °C

3: 1.88 g / 1.) Al-Hg; 2.) AcOH, H₂O / 5 °C / 1.) THF; 2.) 70 min

4: 1.) 2,6-lutidine; 2.) SOCl₂ / CH₂Cl₂ / 1.) -40 deg C; 2.) -40 -> -5 deg C, 30 min

With 2,6-dimethylpyridine; thionyl chloride; aluminium amalgam; water; ozone; acetic acid; triethylamine; In dichloromethane; ethyl acetate; benzene;
DOI:10.1016/S0040-4020(01)97686-0