4-Methylmorpholine → methyl Boc-L-tyrosyl-D-methionyl-glycyl-L-phenylalanyl-3-amino-1-adamantanecarboxylate

Participants

Reaction Steps

To a solution of 3.513 g of methyl D-methionylglycyl-L-phenylalanyl-3-amino-1-adamantanecarboxylate hydrochloride in 30 ml of tetrahydrofuran is added 3.17 g of Boc-L-tyrosine pentachlorophenyl ester followed by 1.12 ml of N-methylmorpholine. The reaction mixture is allowed to stand for 4 hours at room temperature then diluted with 200 ml ethyl acetate. The ethyl acetate layer is separated and washed three times with a 0.5 M solution of potassium bisulfate then dried over magnesium sulfate. The solvent is removed under reduced pressure and the residue is purified by low pressure chromatography on silica gel to give methyl Boc-L-tyrosyl-D-methionyl-glycyl-L-phenylalanyl-3-amino-1-adamantanecarboxylate which is represented by the following formula ##STR19##

Provenance & Evidence