Benzoyl Peroxide → HCID 53807592, compound

HRID 436038Notes

Reaction equation

[C:1]1([CH:7]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[O:8][C:9]([CH:11]([N:15]2[CH:18]([S:19][N:20]3[C:24](=[O:25])[C:23]4=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]4[C:21]3=[O:30])[CH:17]([NH:31][C:32](=[O:41])[CH2:33][O:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:16]2=[O:42])[C:12]([CH3:14])=[CH2:13])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:49]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>ClCCCl>[C:43]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[O:8][C:9]([CH:11]([N:15]2[CH:18]([S:19][N:20]3[C:21](=[O:30])[C:22]4=[CH:29][CH:28]=[CH:27][CH:26]=[C:23]4[C:24]3=[O:25])[CH:17]([NH:31][C:32](=[O:41])[CH2:33][O:34][C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[C:16]2=[O:42])[C:12]([CH2:14][Br:49])=[CH2:13])=[O:10])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 5.6 g (8 mmoles) of 1-(1-diphenylmethoxycarbonyl-2-methylprop-2-enyl)-3-phenoxyacetamido-4-phthalimidothio-azetidin-2-one, 2.8 g (16 mmoles) of N-bromosuccinimide, 150 mg of benzoyl peroxide and 350 ml of 1,2 -dichloroethane was heated in the dark under nitrogen at 80° C for 2.5 hours. After washing with water, drying and concentrating of the reaction mixture, n-hexane was added to the residue to obtain 3 g of crude material which was chromatographed with silica gel [toluene-ethyl acetate 7:1 (v/v)] to obtain 630 mg (0.8 mmole) of 1-(1-diphenylmethoxycarbonyl-2-bromomethylprop-2-enyl)-3-phenoxyacetamido-4-phthalimidothio-azetidin-2-one.

Workup

washAfter washing with water
customdrying
concentrationconcentrating of the reaction mixture, n-hexane
additionwas added to the residue
customto obtain 3 g of crude material which
customwas chromatographed with silica gel [toluene-ethyl acetate 7:1 (v/v)]

Sources & evidence

ORD record: ord-77083dbb42a543f6ae95ebb97aee12e4
Source dataset: uspto-grants-1977_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04007202

Reaction notes

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