Sulfamic Acid → HCID 88683385, compound

HRID 1902917Notes

Reaction equation

HRID 1902917 reaction equation
[CH:1]([NH:3][CH:4]1[C:16](=[O:17])[N:6]2[C:7]([C:13]([OH:15])=[O:14])=[C:8]([CH3:12])[CH2:9][S:10](=[O:11])[C@H:5]12)=[O:2].[CH3:18][Si:19]([CH3:29])([CH3:28])N1CCCCCC1=O.NS(O)(=O)=O.[Br:35]N1C(=O)CCC1=O>ClCCl>[Br:35][CH2:12][C:8]1[CH2:9][S:10](=[O:11])[C@@H:5]2[CH:4]([NH:3][CH:1]=[O:2])[C:16](=[O:17])[N:6]2[C:7]=1[C:13]([O:15][Si:19]([CH3:29])([CH3:28])[CH3:18])=[O:14]

Participants

6

Reactant 4

HCID 5987Sulfamic AcidHCID 67184N-bromobutanimideHCID 114239991-Trimethylsilanyl-azepan-2-oneHCID 88712143HCID 88712143, compound

Product 1

HCID 88683385HCID 88683385, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 357.6 mg (1.39 mmoles) of 7-formamido-3-methyl-3-cephem-4-carboxylic acid-1-oxide in 40 ml of dichloromethane was heated to reflux and 359 mg (1.94 mmoles) of N-trimethylsilylcaprolactam were added thereto to obtain a clear, colorless solution within 3 minutes. This was cooled in an ice-bath and 100 mg (1.02 mmoles) of amidosulfonic acid were added. Bromination was carried out in half an hour using 301.3 mg (1.69 mmoles) of N-bromosuccinimide as the brominating agent to obtain a 62% yield of trimethylsilyl 3-bromomethyl-7-formamido-3-cephem-4-carboxylate-1-oxide.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. customto obtain a clear, colorless solution within 3 minutes
  4. temperatureThis was cooled in an ice-bath
  5. waitBromination was carried out in half an hour

Sources & evidence

ORD record
ord-137169d85f694a548feda0c0ee566038
Source dataset
uspto-grants-1982_12
Patent number
US04366315

Reaction notes

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