Pentachlorophenol → HCID 57205679, compound

Participants

Reaction Conditions

Reaction Steps

1.9 g. (6.2 mmole) of tert.-butyloxycarbonyl-L-methionyl-glycine [M.A. Ondetti, I. Phuscec, E.F. Sabo, J.T. Sheehan, N-Williams; J. Am. Chem. Soc. 92, 195 (1970)] and 1.92 g. (7.2 mmole) of pentachlorophenol are dissolved in 31 ml. of dimethyl formamide. The solution is cooled to 0° C., the solution of 1.41 g. (6.85 mmole) of dicyclohexyl carbodiimide in 6.2 ml. of dimethyl formamide is added dropwise under stirring and the mixture is stirred for a further hour at the same temperature. The mixture is allowed to stand over night; on the following day the precipitated dicyclohexyl urea is filtered off and the filtrate is evaporated to dryness under reduced pressure. The evaporation residue is triturated with ether, the product filtered, washed with a minor amount of ether and recrystallized from a 15-fold amount of ether. 2.19 g. of tert.-butyloxycarbonyl-L-methionyl-glycine pentachlorophenyl ester (63.6% of the theoretical yield) are obtained; m.p. 169°-171° C.; Rf (in the 8:2 mixture of chloroform and ethanol) = 0.8.

Provenance & Evidence