N-bromobutanimide → HCID 70463777, compound

HRID 1902931Notes

Reaction equation

HRID 1902931 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])N1C(=O)CCC1=O.[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 116654792,5-Pyrrolidinedione, 1-(trimethylsilyl)-HCID 70485748HCID 70485748, compound

Product 1

HCID 70463777HCID 70463777, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The clear solution that was obtained after refluxing a mixture of 357 mg (1.02 mmoles) of 3-methyl-7-phenylacetamido-3-cephem-4-carboxylic acid-1-oxide, 50 ml of chloroform and 2 ml (about 10 mmoles) of N-trimethylsilylsuccinimide for one and a half hours was cooled in an ice-bath. Bromination was carried out in half an hour using 0.24 mg (1.35 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. customThe clear solution that was obtained
  2. temperatureafter refluxing
  3. temperaturewas cooled in an ice-bath
  4. waitBromination was carried out in half an hour

Sources & evidence

ORD record
ord-f9d907ec00684e1ea570eb57f1ae2609
Source dataset
uspto-grants-1982_12
Patent number
US04366315

Reaction notes

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