N-bromobutanimide → HCID 54377372, compound

HRID 436037Notes

Reaction equation

HRID 436037 reaction equation
[N+:1]([C:4]1[CH:45]=[CH:44][C:7]([CH2:8][O:9][C:10]([CH:12]([N:16]2[CH:19]([S:20][N:21]3[C:25](=[O:26])[C:24]4=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]4[C:22]3=[O:31])[CH:18]([NH:32][C:33](=[O:42])[CH2:34][O:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:17]2=[O:43])[C:13]([CH3:15])=[CH2:14])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Br:46]N1C(=O)CCC1=O>ClCCCl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10]([CH:12]([N:16]2[CH:19]([S:20][N:21]3[C:22](=[O:31])[C:23]4=[CH:30][CH:29]=[CH:28][CH:27]=[C:24]4[C:25]3=[O:26])[CH:18]([NH:32][C:33](=[O:42])[CH2:34][O:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:17]2=[O:43])[C:13]([CH2:15][Br:46])=[CH2:14])=[O:11])=[CH:44][CH:45]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 54229088HCID 54229088, compound

Product 1

HCID 54377372HCID 54377372, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1.26 g (2 mmoles) of 1-(1p-nitro-benzyloxycarbonyl-2-methylprop-2-enyl)-3-phenoxyacetamido-4-phthalimidothio-azetidin-2-one, 0.71 g (4 mmoles) of N-bromosuccinimide, 50 mg (0.3 mmole) of azoisobutyronitrile and 80 ml of 1,2-dichloroethane was heated in the dark under nitrogen at 70° C for 3 hours. After washing twice with a sodium metabisulfite solution and with water, the reaction mixture was dried and concentrated to a small volume. After treating the residue with hexane, 1.2 g of crude material was isolated which was purified with column chromatography [silica gel, 10:1 (v/v) methylene chloride ethyl acetate] to obtain 0.33 g (0.5 mmole; 23% yield) of 1-(1-p-nitrobenzyloxycarbonyl-2-bromomethylprop-2-enyl)-3-phenoxyacetamido-4-phthalimidothioazetidin-2-one.

Workup

  1. washAfter washing twice with a sodium metabisulfite solution and with water
  2. customthe reaction mixture was dried
  3. concentrationconcentrated to a small volume
  4. additionAfter treating the residue with hexane
  5. custom1.2 g of crude material was isolated which
  6. customwas purified with column chromatography [silica gel, 10:1 (v/v) methylene chloride ethyl acetate]

Sources & evidence

ORD record
ord-8e5fcc5b173745d4a21042c35a1a286a
Source dataset
uspto-grants-1977_02
Patent number
US04007202

Reaction notes

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