Sulfamic Acid → HCID 88683385, compound

HRID 1902916Notes

Reaction equation

HRID 1902916 reaction equation
CN([Si:9]([CH3:12])([CH3:11])[CH3:10])C(=O)C(F)(F)F.[CH:13]([NH:15][CH:16]1[C:28](=[O:29])[N:18]2[C:19]([C:25]([OH:27])=[O:26])=[C:20]([CH3:24])[CH2:21][S:22](=[O:23])[C@H:17]12)=[O:14].NS(O)(=O)=O.[Br:35]N1C(=O)CCC1=O>ClCCl>[Br:35][CH2:24][C:20]1[CH2:21][S:22](=[O:23])[C@@H:17]2[CH:16]([NH:15][CH:13]=[O:14])[C:28](=[O:29])[N:18]2[C:19]=1[C:25]([O:27][Si:9]([CH3:12])([CH3:11])[CH3:10])=[O:26]

Participants

6

Reactant 4

HCID 5987Sulfamic AcidHCID 32510N-methyl-N-(trimethylsilyl)trifluoroacetamideHCID 67184N-bromobutanimideHCID 88712143HCID 88712143, compound

Product 1

HCID 88683385HCID 88683385, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

325 mg (1.63 mmoles) of N-methyl-N-trimethylsilyltrifluoroacetamide were added at room temperature to a suspension of 280.7 mg (1.09 mmoles) of 7-formamido-3-methyl-3-cephem-4-carboxylic acid-1-oxide in 40 ml of dichloromethane and the mixture was stirred for half an hour, after which an almost clear solution was obtained. This was cooled in an ice-bath and 69.5 mg (0.71 mmole) of amidosulfonic acid were added to it. Bromination was carried out in half an hour using 275.8 mg (1.55 mmoles) of N-bromosuccinimide as the brominating agent to obtain a 52% yield of trimethylsilyl 3-bromomethyl-7-formamido-3-cephem-4-carboxylate-1-oxide.

Workup

  1. customafter which an almost clear solution was obtained
  2. temperatureThis was cooled in an ice-bath
  3. waitBromination was carried out in half an hour

Sources & evidence

ORD record
ord-30d60a7b94194ab7a1f6b5e121602ef1
Source dataset
uspto-grants-1982_12
Patent number
US04366315

Reaction notes

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