Trifluoroacetic acid → HCID 6321070, compound

Participants

Reaction Steps

A solution of 0.65 g (0.89 mmol) of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-1-(4-{2-[(tert-butoxycarbonyl)amino]ethoxy}benzyl)-2-hydroxypropylcarbamate in 10 mL of anhydrous CH2Cl2 was treated with 15 mL of TFA and the resulting solution was stirred at RT. After 2 hours the solution was evaporated at reduced pressure and the residue redissolved in CH2Cl2. The solution was washed with 0.5 M aqueous NaOH (1×), water (2×), dried over MgSO4, and concentrated in vacuo. The crude product was purified by flash chromatography (SiO2, 95:5 CH2Cl2/2M NH3 in MeOH) to afford 0.40 g (70%) of the desired compound as a white foam. 1H NMR (CDCl3): 7.39 (dd, 1H), 7.12 (s, 1H), 7.08 (d, 2H), 6.84 (d, 1H), 6.77 (d, 2H), 6.03 (s, 2H), 5.61 (d, 1H), 4.95 (m, 2H), 4.00-3.60 (m, 8H), 3.16-2.62 (m, 10H), 2.20-1.40 (m, 5H), 0.90 (d, 3H), 0.82 (d, 3H). MS(ESI): 636(M+H).

Provenance & Evidence