N-bromobutanimide → HCID 70463777, compound

HRID 1902914Notes

Reaction equation

HRID 1902914 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]([CH3:39])([CH3:38])N1C(=O)C2CCCCC2C1=O.[Br:40]N1C(=O)CCC1=O>ClCCl>[Br:40][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]([CH3:39])([CH3:38])[CH3:25])=[O:9]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 14285102N-trimethylsilylhexahydrophthalimide2×HCID 70485748HCID 70485748, compound

Product 1

HCID 70463777HCID 70463777, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a refluxing suspension of 347 mg (1.00 mmole) of 3-methyl-7-phenylacetamido-3-cephem-4-carboxylic acid-1-oxide in 25 ml of dichloromethane, 340 mg of N-trimethylsilylhexahydrophthalimide (1.5 mmoles) were added and after refluxing for 50 minutes, a second portion of 340 mg of N-trimethylsilylhexahydrophthalimide (1.5 mmoles) was added thereto. The clear solution that was obtained after refluxing for ten minutes was diluted with dichloromethane to approximately 40 ml, was cooled in an ice-bath and then bromination was carried out in one hour using 260 mg (1.46 mmoles) of N-bromosuccinimide as the brominating agent to obtain a 45% yield of of trimethylsilyl 3-bromomethyl-7-phenylacetamido-3-cephem-4-carboxylate-1-oxide.

Workup

  1. additionwere added
  2. temperatureafter refluxing for 50 minutes
  3. customThe clear solution that was obtained
  4. temperatureafter refluxing for ten minutes
  5. temperaturewas cooled in an ice-bath

Sources & evidence

ORD record
ord-2747ccd9b9314584a6e02904a5faaaba
Source dataset
uspto-grants-1982_12
Patent number
US04366315

Reaction notes

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