Sulfamic Acid → HCID 70463777, compound

HRID 1902912Notes

Reaction equation

HRID 1902912 reaction equation
[CH3:1][Si:2]([CH3:12])([CH3:11])N1CCCCCC1=O.[CH3:13][C:14]1[CH2:15][S:16](=[O:36])[C@@H:17]2[CH:24]([NH:25][C:26](=[O:34])[CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:23](=[O:35])[N:18]2[C:19]=1[C:20]([OH:22])=[O:21].NS(O)(=O)=O.[Br:42]N1C(=O)CCC1=O>ClCCl>[Br:42][CH2:13][C:14]1[CH2:15][S:16](=[O:36])[C@@H:17]2[CH:24]([NH:25][C:26](=[O:34])[CH2:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:23](=[O:35])[N:18]2[C:19]=1[C:20]([O:22][Si:2]([CH3:12])([CH3:11])[CH3:1])=[O:21]

Participants

6

Reactant 4

HCID 5987Sulfamic AcidHCID 67184N-bromobutanimideHCID 114239991-Trimethylsilanyl-azepan-2-oneHCID 70485748HCID 70485748, compound

Product 1

HCID 70463777HCID 70463777, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

255 mg of N-trimethylsilylcaprolactam (1.36 mmoles) were added to a refluxing suspension of 360 mg (1.03 mmoles) of 3-methyl-7-phenylacetamido-3-cephem-4-carboxylic acid-1-oxide in 25 ml of dichloromethane and a clear, colorless solution was obtained within 2 minutes. Refluxing was continued for another 25 minutes and the solution was cooled in an ice-bath and diluted to 40 ml with dichloromethane 150 mg of amidosulfonic acid (1.53 mmoles) were added thereto and bromination was carried out in half an hour using 299 mg (1.68 mmoles) of N-bromosuccinimide as the brominating agent to obtain a 51% yield of trimethylsilyl 3-bromomethyl-7-phenylacetamido-3-cephem-4-carboxylate-1-oxide.

Workup

  1. customa clear, colorless solution was obtained within 2 minutes
  2. temperatureRefluxing
  3. temperaturethe solution was cooled in an ice-bath
  4. additionwere added
  5. waitbromination was carried out in half an hour

Sources & evidence

ORD record
ord-901ed1fc421e44b78af5e6eded5543cb
Source dataset
uspto-grants-1982_12
Patent number
US04366315

Reaction notes

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