Phenylacetyl chloride → HCID 70575130, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 1.53 g (0.002 mole) of benzyl 6-amino-1'-phenyl-spiro[penam-2,4'-piperidine]-3-carboxylate di-p-toluenesulfonate (prepared according to the method described in Example 1.8.3. of our Application Ser. No. 06/162,616, filed June 24, 1980) in 100 ml of anhydrous dichloromethane is added all at once 404 mg (0.004 mole) of triethylamine in 10 ml of dichloromethane. The solution is cooled to a temperature of from 0° to -5° C. and then there are simultaneously added dropwise a solution of 340 mg (0.022 mole) of phenylacetyl chloride in 30 ml of dichloroemethane and a solution of 220 mg (0.022 mole) of triethylamine in 30 ml of dichloromethane, the addition taking place over the course of about 1 hour. Thereafter, the reaction mixture is stirred for 3 hours at 15° C., then successively washed with water, with a saturated aqueous solution of sodium hydrogen carbonate and again with water. After evaporating the solution to dryness and recrystallizing the residue from ethyl acetate/hexane (1:3 v/v), there are obtained 950 mg of benzyl 1'-phenyl-6-(2-phenylacetamido)-spiro[penam-2,4'-piperidine]-3-carboxylate. Yield: 88%; M.P. 120°-121° C.

Provenance & Evidence