N-bromobutanimide → HCID 70463777, compound

HRID 1902926Notes

Reaction equation

HRID 1902926 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]([CH3:34])([CH3:33])N1CCOC1=O.[Br:35]N1C(=O)CCC1=O>ClCCl>[Br:35][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]([CH3:34])([CH3:33])[CH3:25])=[O:9]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 1235143-(Trimethylsilyl)oxazolidin-2-oneHCID 70485748HCID 70485748, compound

Product 1

HCID 70463777HCID 70463777, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture consisting of 753 mg (2.16 mmoles) of 3-methyl-7-phenylacetamido-3-cephem-4-carboxylic acid-1-oxide, 785 mg (4.94 mmoles) of N-trimethylsilyl-2-oxazolidinone and 70 ml of dichloromethane was refluxed for 2 hours, after which a clear, almost colorless solution was obtained. This was cooled in an ice-bath and bromination was carried out in half an hour using 624.5 mg (3.51 mmoles) of N-bromosuccinimide as the brominating agent to obtain a yield of 48% of trimethylsilyl 3-bromomethyl-7-phenylacetamido-3-cephem-4-carboxylate-1-oxide.

Workup

  1. temperaturewas refluxed for 2 hours
  2. customafter which a clear, almost colorless solution was obtained
  3. temperatureThis was cooled in an ice-bath
  4. waitbromination was carried out in half an hour

Sources & evidence

ORD record
ord-0afbe585a15b4d9b8509773fcce1d469
Source dataset
uspto-grants-1982_12
Patent number
US04366315

Reaction notes

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