N-bromobutanimide → HCID 70463777, compound

HRID 1902930Notes

Reaction equation

HRID 1902930 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]([CH3:35])([CH3:34])NC(=O)C(C)(C)C.[Br:36]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:36][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]([CH3:35])([CH3:34])[CH3:25])=[O:9]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 10931917HCID 10931917, compoundHCID 70485748HCID 70485748, compound

Product 1

HCID 70463777HCID 70463777, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

352 mg (1.01 mmoles) of 3-methyl-7-phenylacetamido-3-cephem-4-carboxylic acid-1-oxide were silylated in 40 ml of chloroform at 60° C. in half an hour with 0.28 g (1.8 mmoles) of N-trimethylsilyl-2,2-dimethylpropanamide and the clear, pale yellow solution obtained was cooled in an ice-bath. Bromination was carried out in half an hour using 0.24 g (1.35 mmoles) of N-bromosuccinimide as the brominating agent to obtain a 40% yield of trimethylsilyl 3-bromomethyl-7-phenylacetamido-3-cephem-4-carboxylate-1-oxide.

Workup

  1. customthe clear, pale yellow solution obtained
  2. temperaturewas cooled in an ice-bath
  3. waitBromination was carried out in half an hour

Sources & evidence

ORD record
ord-78966b3ad60f411f9a9000ec23a28bac
Source dataset
uspto-grants-1982_12
Patent number
US04366315

Reaction notes

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