N-bromobutanimide → HCID 70463777, compound

HRID 1902934Notes

Reaction equation

HRID 1902934 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]([CH3:38])([CH3:37])NS(C1C=CC=CC=1)(=O)=O.[Br:39]N1C(=O)CCC1=O>ClCCl>[Br:39][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]([CH3:38])([CH3:37])[CH3:25])=[O:9]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 12271451N-(Trimethylsilyl)benzenesulfonamide2×HCID 70485748HCID 70485748, compound

Product 1

HCID 70463777HCID 70463777, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

352 mg (1.01 mmoles) of 3-methyl-7-phenylacetamido-3-cephem-4-carboxylic acid-1-oxide were added to a solution of 0.45 mg (2.0 mmoles) of N-trimethylsilylbenzenesulfonamide in 70 ml of dichloromethane and after refluxing for half an hour a still slightly turbid solution was obtained. An additional 0.42 g of N-trimethylsilylbenzenesulfonamide (1.8 mmoles) was added and refluxing was continued for half an hour. The clear, light yellow solution obtained was cooled in an ice-bath and bromination was carried out in one hour using 0.26 mg (1.46 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. temperatureafter refluxing for half an hour a still slightly turbid solution
  2. customwas obtained
  3. temperaturerefluxing
  4. waitwas continued for half an hour
  5. customThe clear, light yellow solution obtained
  6. temperaturewas cooled in an ice-bath

Sources & evidence

ORD record
ord-78fa7ed55cec4ec398e02fddc6d664bd
Source dataset
uspto-grants-1982_12
Patent number
US04366315

Reaction notes

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