反应详情

To a solution of (1S,2S)-2-{[(benzyloxy)carbonyl]amino}-3-[-(3,3-diethoxypropyl)amino]-1-methyl-3-oxopropyl myristate (1.06 g, 1.79 mmol, obtained from Reference Example 47) in anhydrous tetrahydrofuran was added 0.5 N hydrochloric acid (4.3 ml). The resulting solution was stirred at room temperature for 5 hours. The reaction mixture was brought to pH 9 with aqueous sodium bicarbonate, extracted with ethyl acetate (3×75 ml), the combined organics were washed with saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was chromatographed (flash column, silica gel, 45% ethyl acetate in hexane) to provide (1S,2S)-2-{[(benzyloxy)carbonyl]amino}-1-methyl-3-oxo-3-[(3-oxopropyl)amino]propyl myristate (694 mg, 75%) as a white solid.

1. extractionextracted with ethyl acetate (3×75 ml)
2. washthe combined organics were washed with saturated sodium chloride
3. dry with materialdried over magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customThe residue was chromatographed (flash column, silica gel, 45% ethyl acetate in hexane)