Water → N-(4-oxo-1-adamantyl)acetamide

Participants

Reaction Steps

A solution of 1.2 g of nitryltetrafluoroborate in 15 ml of acetonitrile is cooled to 0° C. and a solution of 2.17 g of 5-bromo-2-oxoadamantane [preparation is described in H. W. Geluk, SYNTHESIS, p. 374 (1972)] in 15 ml of acetonitrile is added with rapid stirring and cooling. The reaction mixture is stirred for 30 minutes then poured into water and extracted with diethyl ether. The diethyl ether extract is washed with 5% sodium bicarbonate solution and water and dried over magnesium sulfate. The solvent is removed under reduced pressure to give N-(2-oxoadamantan-5-yl)acetamide. Substitution of an equivalent quantity of N-(2-oxoadamantan-5-yl)acetamide for the methyl 2-oxoadamantane-1-carbamate of Example 57 and substantial repetition of the procedures detailed therein provides methyl L-tyrosyl-D-methionylglycyl-L-phenylalanyl-5-amino-2-adamantanecarboxylate hydrochloride which is represented by the formula ##STR68##

Provenance & Evidence