2,2,2-Trichloroethyl 2-chloromethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate → 2,2,2-Trichloroethyl 7-(2-phenylacetamido)-3-methyl-3-cephem-4-carboxylate
Reaction equation
[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:28](=[O:29])[N:13]3[CH:14]([C:20]([O:22][CH2:23][C:24]([Cl:27])([Cl:26])[Cl:25])=[O:21])[C:15]([CH3:19])([CH2:17]Cl)[S:16][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>N1C=CC=CC=1>[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:28](=[O:29])[N:13]3[C:14]([C:20]([O:22][CH2:23][C:24]([Cl:27])([Cl:25])[Cl:26])=[O:21])=[C:15]([CH3:19])[CH2:17][S:16][C@H:12]23)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
3
Procedure
A mixture of 2,2,2-trichloroethyl 6-(2-phenylacetamido)-2-methyl-2-chloromethylpenam-3-carboxylate (0.50 g.) in 1,1,2-trichloroethane(7 cc) and pyridine (0.16 g.) was heated under reflux for 3.5 hours. After cooling the reaction mixture was washed with water, dried and then concentrated under reduced pressure. The residue was subjected to chromatography on silica gel and eluated with chloroform. The eluate was concentrated and the residue was crystalized with ether to yield crystals (0.12 g.) of 2,2,2-trichloroethyl 7-(2-phenylacetamido)-3-methyl-3-cephem-4-carboxylate, m.p. 161°-162° C.
Workup
- temperaturewas heated
- temperatureunder reflux for 3.5 hours
- temperatureAfter cooling the reaction mixture
- washwas washed with water
- customdried
- concentrationconcentrated under reduced pressure
- concentrationThe eluate was concentrated
- customthe residue was crystalized with ether
Sources & evidence
- ORD record
- ord-7a8938c63f5c4ba2bb4d0f4959054ba2
- Source dataset
- uspto-grants-1983_10
- Patent number
- US04410458
Reaction notes
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