Dicyclohexylcarbodiimide → (1S,2S)-2-{[(benzyloxy)carbonyl]amino}-3-[(3,3-diethoxypropyl)amino]-1-methyl-3-oxopropyl myristate

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Reaction Steps

To a solution of [(1S,2S)-1-(3,3-diethoxy-propylcarbamoyl)-2-hydroxy-propyl]carbamic acid benzyl ester (300 mg, 0.785 mmol, obtained from Reference Example 17) in methylene chloride (5 ml) was added myristic acid (163 mg, 0.714 mmol), dicyclohexylcarbodiimide (162 mg, 0.785 mmol) and dimethylaminopyridine (9 mg, 0.074 mmol). The resulting mixture was stirred under nitrogen at room temperature for 18 hours. The mixture was filtered, the filtrate was washed with 2% hydrochloric acid, aqueous sodium bicarbonate and saturated sodium chloride solutions, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was chromatographed (flash column, silica gel, 30% ethyl acetate in hexane) to provide (1S,2S)-2-{[(benzyloxy)carbonyl]amino}-3-[(3,3-diethoxypropyl)amino]-1-methyl-3-oxopropyl myristate (352 mg, 83%) as a white solid.

Provenance & Evidence