Ammonia → HCID 66551358, compound

Participants

Reaction Steps

A solution of (3aR,5R,6S,7R,7aR)-5-(acetoxymethyl)-2-(2-cyclopropylethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diyl diacetate (15 g, 36 mmol) in MeOH (400 mL) was bubbled with NH3(g) for 2 h. After stirred overnight at room temperature, the reaction mixture was condensed to give a residue, which was washed with hot ethyl acetate to provide the title compound as a white solid (9 g, 86%). (ES, m/z): [M+H]+289.0; 1H NMR (300 MHz, CDCl3) δ 6.18-6.20 (d, J=6.3 Hz, 1H), 4.10-4.12 (m, 1H), 3.93-3.97 (m, 1H), 3.70-3.75 (m, 1H), 3.47-3.62 (m, 3H), 3.20-3.25 (m, 2H), 1.32-1.38 (m, 2H), 0.61-0.65 (m, 1H), 0.36-0.37 (m, 2H), 0.08-0.12 (m, 2H).

Provenance & Evidence