Sulfamic Acid → HCID 70463777, compound

HRID 1902932Notes

Reaction equation

HRID 1902932 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]([CH3:37])([CH3:36])NC(=O)C1C=CC=CC=1.NS(O)(=O)=O.[Br:43]N1C(=O)CCC1=O>ClCCl>[Br:43][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]([CH3:37])([CH3:36])[CH3:25])=[O:9]

Participants

6

Reactant 4

HCID 5987Sulfamic AcidHCID 67184N-bromobutanimideHCID 601133N-trimethylsilylbenzamideHCID 70485748HCID 70485748, compound

Product 1

HCID 70463777HCID 70463777, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

601.5 mg (1.73 mmoles) of 3-methyl-7-phenylacetamido-3-cephem-4-carboxylic acid-1-oxide were silylated by refluxing in 50 ml of dichloromethane for one hour with 503 mg (2.61 mmoles) of N-trimethylsilylbenzamide. 0.1 g of amidosulfonic acid (1 mmole) were added to the clear, slightly yellow solution obtained and after cooling in an ice-bath, bromination was carried out in half an hour with 464.8 mg (2.61 mmoles) of N-bromosuccinimide to obtain a yield of 42% of trimethylsilyl 3-bromomethyl-7-phenylacetamido-3-cephem-4-carboxylate-1-oxide.

Workup

  1. customobtained
  2. temperatureafter cooling in an ice-bath

Sources & evidence

ORD record
ord-a3c443d974a44dfe8cd16052513910be
Source dataset
uspto-grants-1982_12
Patent number
US04366315

Reaction notes

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