Triethylamine → HCID 86701115, compound

Participants

Reaction Steps

To a solution of ((3aR,5R,6S,7R,7aR)-6,7-bis(benzyloxy)-2-(dimethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-5-yl)methanol (94) (8 g, 18 mmol) (Prepared according to the synthesis of Example 149, step 2) in dichloromethane (50 mL) was added methanesulfonyl chloride (4.3 g, 37 mmol) and triethylamine (3.8 g, 37 mmol) at 0° C. After kept 2 hours at 25° C., the reaction was quenched by water (50 mL) and extracted with dichloromethane (3×50 mL). The combined organic layer was washed with brine (2×30 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give a residue, which was purified by a silica gel column, eluted with 20%-30% ethyl acetate in petroleum ether to afford the title compound as a brown syrup (8.5 g, 90%); (ES, m/z) [M+H]+ 507.0; 1HNMR (300 MHz, CDCl3) δ 7.28-7.48 (m, 10H), 6.38 (d, J=6.6 Hz, 1H), 5.04-5.08 (m, 1H), 4.72-4.86 (m, 4H), 4.19-4.24 (m, 3H), 3.70-3.83 (m, 1H), 3.56-3.58 (m, 1H), 3.19 (s, 3H), 2.94 (s, 6H).

Provenance & Evidence