Ammonium fluoride → HCID 58959766, compound

Participants

Reaction Conditions

Reaction Steps

Ammonium fluoride (2.80 g, 75.5 mmol) was added in one portion to a solution of methyl-3-(3-{(2R)-2-[(2R)-2-{[tert-Butyl(dimethyl)silyl]oxy}-2-(4-[benzyloxy]-3-hydroxymethyl-phenyl)-ethylamino]-propyl}-phenyl)-propanoate (Preparation 53) (4.47 g, 7.55 mmol) in water (20 ml) and methanol (30 ml) at room temperature. The reaction was heated at 40° C. for 18 hours and then allowed to cool to room temperature. The methanol was removed in vacuo and the resulting aqueous extracted with dichloromethane (3×75 ml), the combined organics were washed with water (25 ml), dried (sodium sulfate) and the solvent removed in vacuo to yield an orange foam. This was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol: 880 ammonia (95:5:0.5 by volume) to give the title compound as a yellow oil (3.21 g).

Provenance & Evidence