Acetamide, N-(trimethylsilyl)- → HCID 70463777, compound

HRID 1902909Notes

Reaction equation

HRID 1902909 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]([CH3:32])([CH3:31])NC(=O)C.[Br:33]N1C(=O)CCC1=O>ClCCl>[Br:33][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]([CH3:32])([CH3:31])[CH3:25])=[O:9]

Participants

5

Reactant 3

HCID 25989Acetamide, N-(trimethylsilyl)-HCID 67184N-bromobutanimideHCID 70485748HCID 70485748, compound

Product 1

HCID 70463777HCID 70463777, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a refluxing suspension of 359 mg (1.03 mmoles) of 3-methyl-7-phenylacetamido-3-cephem-4-carboxylic acid-1-oxide in 25 ml of dichloromethane, 189 mg of N-trimethylsilylacetamide (1.45 mmoles) were added and the clear solution that was obtained after refluxing for 3/4 hours was cooled in an ice-bath and diluted to 40 ml with dichloromethane. Bromination was carried out in half an hour using 287 mg (1.61 mmoles) of N-bromosuccinimide as the brominating agent to obtain a yield of 46% of trimethylsilyl 3-bromomethyl-7-phenylacetamido-3-cephem-4-carboxylate-1-oxide.

Workup

  1. additionwere added
  2. customthe clear solution that was obtained
  3. temperatureafter refluxing for 3/4 hours
  4. temperaturewas cooled in an ice-bath
  5. waitBromination was carried out in half an hour

Sources & evidence

ORD record
ord-33956dc920a4460a9071d3544561d8fd
Source dataset
uspto-grants-1982_12
Patent number
US04366315

Reaction notes

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