4-Amino-2-fiuorobenzoylglutamic acid di-t-butyl ester → 4-(6,7-Bis(palmitoyloxy)-4-thiaheptanoyl)amino-2-fluorobenzoylglutamic acid di-t-butyl ester

Participants

Reaction Steps

To a solution of 4-amino-2-fiuorobenzoylglutamic acid di-t-butyl ester (181 mg) in pyridine (2.3 ml), phosphorus trichloride (0.020 ml) was added, followed by stirring at room temperature for 2 hours. To this mixture, 6,7-bis(palmitoyloxy)-4-thiaheptanoic acid as obtained in Reference Example 24 (150 mg) was added, followed by stirring at room temperature for 24 hours. The reaction mixture was diluted with water, extracted with ethyl acetate. The extract was washed with a 5% aqueous solution of citric acid, a saturated aqueous solution of sodium hydrogen carbonate and saturated saline, and dried over anhydrous sodium sulfate, and the solvent was distilled off. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to yield the title compound (205 mg, yield 87%) as a wax-like substance.

Provenance & Evidence