Sulfamic Acid → Trimethylsilyl 3-bromomethyl-7-phenylacetamido-3-cephem-4-carboxylic acid-1-oxide
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>[CH3:25][Si:26]([CH:3]1[C:2]([CH2:1][Br:38])=[C:7]([C:8]([OH:10])=[O:9])[N:6]2[C:11](=[O:23])[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@H:5]2[S:4]1=[O:24])([CH3:32])[CH3:31]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
342 mg (0.98 mmole) of 3-methyl-7-phenylacetamido-3-cephem-4-carboxylic acid-1-oxide were suspended in 25 ml of dichloromethane and the mixture was heated to refluxed 157 mg of N-trimethylsilylacetamide (1.20 mmoles) were added thereto and refluxing was continued for 3/4 hour. To the clear, colorless solution obtained, 50 mg of amidosulfonic acid (0.51 mmoles) were added and the mixture was diluted to 40 ml with dichloromethane. The ice-cooled solution was brominated in half an hour using 280 mg (1.57 mmoles) of N-bromosuccinimide as the brominating agent to obtain a yield of 49% of trimethylsilyl 3-bromomethyl-7-phenylacetamido-3-cephem-4-carboxylic acid-1-oxide.
Workup
- temperaturethe mixture was heated
- additionwere added
- temperaturerefluxing
- waitwas continued for 3/4 hour
- customTo the clear, colorless solution obtained
- waitwas brominated in half an hour
Sources & evidence
- ORD record
- ord-28689f7c240a4199b041cded73d72031
- Source dataset
- uspto-grants-1982_12
- Patent number
- US04366315
Reaction notes
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