Ammonium fluoride → HCID 57978218, compound

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Reaction Steps

A solution of methyl 3-{(2R)-2-[((2R)-2-[4-(benzyloxy)-3-(hydroxymethyl)phenyl]-2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)amino]propyl}benzoate (Preparation 62) (10 g, 17.74 mmol) and ammonium fluoride (6.57 g, 177 mmol) in methanol (180 ml) and water (60 ml) was heated at 40° C. for 18 hrs. The methanol was removed in vacuo and the remaining aqueous layer extracted with dichloromethane (2×100 ml). The combined organic layers were dried (sodium sulfate), filtered and evaporated in vacuo. The resulting oil 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 (6.83 g) as a pale yellow gum. 1H NMR (400 MHz, CD3OD): δ=7.83-7.82 (1H, d), 7.78 (1H, s), 7.47-7.45 (2H, m), 7.39-7.28 (6H, m), 7.11-7.10 (1H, d), 6.89-6.87 (1H, d), 5.11 (2H, s), 4.65 (2H, s), 4.65-4.62 (1H, m), 3.88 (3H, s), 2.98-2.89 (2H, m), 2.79-2.64 (3H, m), 1.09-1.08 (3H, d) ppm. LRMS (electrospray): m/z [M+H]+ 450, [M+Na]+ 472, [M−H]− 448.

Provenance & Evidence