m-Chloroperbenzoic acid → p-Nitrobenzyl 2-(4-ethylsulfinyl-2-oxo-1-azetidinyl)-3-acetylthio-3-(2-ethoxyethylthio)acrylate

HRID 4434Notes

Reaction equation

[CH2:1]([S:3][CH:4]1[N:7]([C:8](=[C:22]([S:29][C:30](=[O:32])[CH3:31])[S:23][CH2:24][CH2:25][O:26][CH2:27][CH3:28])[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)=[O:10])[C:6](=[O:33])[CH2:5]1)[CH3:2].ClC1C=CC=C(C(OO)=[O:42])C=1>C(Cl)Cl>[CH2:1]([S:3]([CH:4]1[N:7]([C:8](=[C:22]([S:29][C:30](=[O:32])[CH3:31])[S:23][CH2:24][CH2:25][O:26][CH2:27][CH3:28])[C:9]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=2)=[O:10])[C:6](=[O:33])[CH2:5]1)=[O:42])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 1.4 g p-nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-3-acetylthio-3-(2-ethoxyethylthio)-acrylate in 75 ml. methylene chloride was cooled to 0° C. under a nitrogen atmosphere. A solution of 0.551 g m-chloroperbenzoic acid in 25 ml methylene chloride was added dropwise, then the reaction mixture was stirred at 0° C. for 1 hour. The methylene chloride solution was then washed with two 25 ml portions of saturated aqueous sodium bicarbonate solution and two 25 ml portions of water, dried over anhydrous sodium sulfate and concentrated in vacuo to an oil. The crude title compound (1.25 g) was used without further purification. The NMR spectrum of a deuterochloroform solution showed peaks at 1.24(m, 6H); 2.27-3.74(c, 13H); 4.7-5.46 (c, 3H); 7.57(m, 2H); and 8.23(m, 2H) ppm. The infrared spectrum of a dichloromethane solution has absorption bands at 5.6 and 5.79 microns.

Workup

washThe methylene chloride solution was then washed with two 25 ml portions of saturated aqueous sodium bicarbonate solution and two 25 ml portions of water
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo to an oil
customThe crude title compound (1.25 g) was used without further purification
customabsorption bands at 5.6 and 5.79 microns

Sources & evidence

ORD record: ord-0390e1237c0d4ce1b863fbe6e79e9218
Source dataset: uspto-grants-1988_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04725678

Reaction notes

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