Trifluoroacetic acid → HCID 14130750, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (3R,4R,5S,6R)-6-(acetoxymethyl)-3-isothiocyanato-tetrahydro-2H-pyran-2,4,5-triyltriacetate (59 g, 151 mmol) in dichloromethane (500 mL) was added propan-1-amine (9.4 g, 159 mmol) dropwise with stirring at 0° C. After stirred for 1 h, the reaction solution was treated with trifluoroacetic acid (130 g, 1.34 mol) overnight at room temperature. The reaction mixture was washed with saturated sodium bicarbonate (300 mL), dried over anhydrous magnesium sulfate, and concentrated under vacuum to provide a residue, which was purified by silica gel column, eluted with 1% MeOH in dichloromethane to give compound 14 as a yellow oil (50 g, 84%). (ES, m/z): [M+H]+ 388.9; 1H NMR (300 MHz, CDCl3) δ 6.14-6.16 (d, J=6.6 Hz, 1H), 5.33-5.35 (m, 1H), 5.05-5.19 (m, 1H), 4.85-4.89 (m, 1H), 4.27-4.30 (m, 1H), 4.08 (s, 2H), 3.75-3.81 (m, 1H), 3.06-3.28 (m, 2H), 1.97-2.04 (m, 9H), 1.49-1.58 (m, 2H), 0.82-0.91 (m, 3H).

Provenance & Evidence