Methanol → 2,2,2-Trichloroethyl 2-bromomethyl-2-methyl-6-aminopenam-3-carboxylate hydrochloride

HRID 1075991Notes

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]1

Participants

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 (6.5 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). Infrared Absorption Spectrum (Nujol) 3350 ~3400, 1790, 1770 cm-1.

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-6818125939774cc6854fc744938dcf23
Source dataset: uspto-grants-1976_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03954732

Reaction notes

Loading…