Sodium Hydroxide → HCID 68175019, compound

Participants

Reaction Steps

Tin(II) chloride dihydrate (2.06 g) was added to a suspension of tert-butyl ((4aS,5S,7aS)-7a-(2,3-difluoro-5-nitrophenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)carbamate, obtained in Preparation Example 2-(29), (1.17 g) in ethanol (20 ml) at RT. The mixture was stirred for 16 h at the same temperature (the solid gradually dissolved and the reaction color became yellow). The resultant mixture was poured into 2N sodium hydroxide solution and the organic was extracted with EtOAc. The organic layer was washed sequentially with water and brine, then dried over MgSO4. The solid was removed by filtration, and the filtrate was concentrated in vacuo. The crude mixture was purified by silica gel column chromatography (gradient from 20% to 60% EtOAc in heptane) acetate to afford the targeted compound (1.09 g) as a pale yellow solid. 1H-NMR (400 MHz, CDCl3) δ (ppm): 1.51 (s, 9H), 2.69-2.73 (m, 1H), 3.07-3.15 (m, 2H), 3.69 (bs, 2H), 3.84-3.85 (m, 1H), 4.49-4.67 (m, 4H), 6.34-6.36 (m, 1H), 6.44 (ddd, J=11.2, 6.4, 2.8 Hz, 1H)

Provenance & Evidence