N-bromobutanimide → HCID 70463777, compound

HRID 1902925Notes

Reaction equation

HRID 1902925 reaction equation
[CH3:1][C:2]1[CH2:3][S:4](=[O:24])[C@@H:5]2[CH:12]([NH:13][C:14](=[O:22])[CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:11](=[O:23])[N:6]2[C:7]=1[C:8]([OH:10])=[O:9].[CH3:25][Si:26]([CH3:37])([CH3:36])NC(=O)C1C=CC=CC=1.[Br:38]N1C(=O)CCC1=O>ClCCl>[Br:38][CH2:1][C:2]1[CH2:3][S:4](=[O:24])[C@@H:5]2[CH:12]([NH:13][C:14](=[O:22])[CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:11](=[O:23])[N:6]2[C:7]=1[C:8]([O:10][Si:26]([CH3:37])([CH3:36])[CH3:25])=[O:9]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 601133N-trimethylsilylbenzamideHCID 70485748HCID 70485748, compound

Product 1

HCID 70463777HCID 70463777, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

458 mg of 3-methyl-7-phenylacetamido-3-cephem-4-carboxylic acid-1-oxide (1.32 mmoles) were silylated in 40 ml of dichloromethane with 397 mg (2.06 mmoles) of N-trimethylsilylbenzamide by refluxing for half an hour and the clear, pale yellow solution was cooled in an ice-bath. Bromination was carried out in half an hour with 378.5 mg (2.13 mmoles) of N-bromosuccinimide as the brominating agent to obtain a 42% yield of trimethylsilyl 3-bromomethyl-7-phenylacetamido-3-cephem-4-carboxylate-1-oxide.

Workup

  1. temperatureby refluxing for half an hour
  2. temperaturethe clear, pale yellow solution was cooled in an ice-bath

Sources & evidence

ORD record
ord-bfc9e3078c2348f8ada8f7cf3e35dfe4
Source dataset
uspto-grants-1982_12
Patent number
US04366315

Reaction notes

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