Reaktion #96120

Reaktionsgleichung

2,2,2-trichloroethyl α-[4-cyclopropylmethoxycarbonylthio-3-phenoxyacetamido-2-oxoazetidine-1-yl]-α-(2-bromo-1-hydroxyethylidene)acetate

aluminum chloride

→

2,2,2-trichloroethyl 7-phenoxyacetamido-3-oxocepham-4-carboxylate

Ausbeute 124.7%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONThe reaction mixture is poured into ice cold diluted hydrochloric acid
2. 2
   Extraktionis extracted with ethyl acetate
3. 3
   WaschenThe extract solution is washed with diluted hydrochloric acid and water
4. 4
   Sonstigedried
5. 5
   Sonstigeevaporated

Vorschrift

To a stirred solution of 2,2,2-trichloroethyl α-[4-cyclopropylmethoxycarbonylthio-3-phenoxyacetamido-2-oxoazetidine-1-yl]-α-(2-bromo-1-hydroxyethylidene)acetate (330 mg) in methylene chloride (6 ml) is added aluminum chloride (330 mg) at room temperature, and the mixture is stirred for 60 minutes. The reaction mixture is poured into ice cold diluted hydrochloric acid, and is extracted with ethyl acetate. The extract solution is washed with diluted hydrochloric acid and water, dried, and evaporated to give 2,2,2-trichloroethyl 7-phenoxyacetamido-3-oxocepham-4-carboxylate (300 mg). Foam. IR: νmaxCHCl3 3420, 1780, 1685 cm-1. NMR: δCDCl3 3.37s2H, 4.53s2H, 4.85s2H, 5.07d(4)1H, 5.20-5.73m2H, 6.8-7.7m6H.

Quelle