N-bromobutanimide → HCID 70463777, compound

HRID 1902928Notes

Reaction equation

HRID 1902928 reaction equation
[CH3:1][Si:2]([CH3:11])([CH3:10])NC(=O)C(C)(C)C.[CH3:12][C:13]1[CH2:14][S:15](=[O:35])[C@@H:16]2[CH:23]([NH:24][C:25](=[O:33])[CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:22](=[O:34])[N:17]2[C:18]=1[C:19]([OH:21])=[O:20].[Br:36]N1C(=O)CCC1=O>ClCCl.[N+](C1C=CC=CC=1)([O-])=O>[Br:36][CH2:12][C:13]1[CH2:14][S:15](=[O:35])[C@@H:16]2[CH:23]([NH:24][C:25](=[O:33])[CH2:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:22](=[O:34])[N:17]2[C:18]=1[C:19]([O:21][Si:2]([CH3:11])([CH3:10])[CH3:1])=[O:20]

Participants

6

Reactant 3

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

Product 1

HCID 70463777HCID 70463777, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7416NitrobenzeneSolvent

Procedure

355.9 mg (2.06 mmoles) of N-trimethylsilyl-2,2-dimethylpropanamide were added to a suspension of 426.0 mg (1.22 mmoles) of 3-methyl-7-phenylacetamido-3-cephem-4-carboxylic acid-1-oxide in a mixture of 40 ml of dichloromethane and 2 ml of nitrobenzene and the mixture obtained was refluxed for one hour. The clear solution obtained was cooled in an ice-bath and bromination was carried out in half an hour using 336.6 mg (1.89 mmoles) of N-bromosuccinimide as the brominating agent to obtain a 44% yield of trimethylsilyl 3-bromomethyl-7-phenylacetamido-3-cephem-4-carboxylate-1-oxide.

Workup

  1. customthe mixture obtained
  2. temperaturewas refluxed for one hour
  3. customThe clear solution obtained
  4. temperaturewas cooled in an ice-bath
  5. waitbromination was carried out in half an hour

Sources & evidence

ORD record
ord-8865a52ffc644a06965c3302a50f8efe
Source dataset
uspto-grants-1982_12
Patent number
US04366315

Reaction notes

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