Methanol → 2,2,2-Trichloroethyl 2-bromomethyl-2-methyl-6-aminopenam-3-carboxylate hydrochloride
Reaction equation
[Br:1][CH2:2][C:3]1([CH3:29])[CH:7]([C:8]([O:10][CH2:11][C:12]([Cl:15])([Cl:14])[Cl:13])=[O:9])[N:6]2[C:16](=[O:28])[CH:17]([NH:18]C(=O)CC3C=CC=CC=3)[C@H:5]2[S:4]1.CN(C)C1C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl.CO>C(Cl)Cl.O>[ClH:13].[Br:1][CH2:2][C:3]1([CH3:29])[CH:7]([C:8]([O:10][CH2:11][C:12]([Cl:15])([Cl:14])[Cl:13])=[O:9])[N:6]2[C:16](=[O:28])[CH:17]([NH2:18])[C@H:5]2[S:4]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -15 °C
Procedure
2,2,2-Trichloroethyl 2-bromomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate (10.8 g) was dissolved in dried methylene chloride (300 ml). To this solution were added under cooling at -35° C dried dimethylaniline (3.6 g) and then phosphorus pentachloride (6.4 g) and the mixture was stirred for 2.5 hours at the same temperature. To the solution was added dropwise anhydrous methanol (6.4 g) at the same temperature and the mixture was stirred for 1 hour at -15° C. Water (6.3 ml) was added to the solution and the solution was vigorously stirred for 30 minutes. After the reaction, precipitates were collected by filtration, washed with methylene chloride and further with ether and then dried to give powdery 2,2,2-trichloroethyl 2-bromomethyl-2-methyl-6-aminopenam-3-carboxylate hydrochloride (7.8 g).
Workup
- additionTo this solution were added
- stirringthe solution was vigorously stirred for 30 minutes
- customAfter the reaction
- customprecipitates
- filtrationwere collected by filtration
- washwashed with methylene chloride and further with ether
- customdried
Sources & evidence
- ORD record
- ord-1648e6d391644f98a568eaa0f3b4694c
- Source dataset
- uspto-grants-1977_11
- Patent number
- US04056521
Reaction notes
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