Sulfamic Acid → HCID 70463777, compound

HRID 1902911Notes

Reaction equation

HRID 1902911 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.NS(O)(=O)=O.[Br:38]N1C(=O)CCC1=O>ClCCl>[Br:38][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

6

Reactant 4

HCID 5987Sulfamic AcidHCID 25989Acetamide, N-(trimethylsilyl)-HCID 67184N-bromobutanimideHCID 70485748HCID 70485748, compound

Product 1

HCID 70463777HCID 70463777, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a refluxing suspension of 329 mg (0.95 mmole) of 3-methyl-7-phenylacetamido-3-cephem-4-carboxylic acid-1-oxide in 25 ml of dichloromethane, 298 mg (2.27 mmoles) of N-trimethylsilylacetamide were added and a clear, colorless solution was obtained after 15 minutes. Refluxing was continued for another 30 minutes after which 300 mg (3.06 mmoles) of amidosulfonic acid were added. The mixture was diluted with dichloromethane to 40 ml and cooled in an ice-bath. Bromination was carried out in one hour using 280 mg (1.57 mmoles) of N-bromosuccinimide as the brominating agent to obtain a yield of 50% of trimethylsilyl 3-bromomethyl-7-phenylacetamido-3-cephem-4-carboxylate-1-oxide.

Workup

  1. additionwere added
  2. customa clear, colorless solution was obtained after 15 minutes
  3. temperatureRefluxing
  4. temperaturecooled in an ice-bath
  5. waitBromination was carried out in one hour

Sources & evidence

ORD record
ord-8f47359f58374c548a9c2855285f9a62
Source dataset
uspto-grants-1982_12
Patent number
US04366315

Reaction notes

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