Sodium Azide → HCID 86762147, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of tert-butyl ((4aR,7aR)-7a-(5-bromo-2-fluorophenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-yl)carbamate (300 mg, 0.696 mmol), sodium azide (274 mg, 4.21 mmol), trans-1,2-(bismethylamino)cyclohexane (0.073 mL, 0.464 mmol), 0.66 M aqueous L-ascorbic acid sodium salt (0.780 mL, 0.515 mmol) and 0.33 M aqueous copper(II) sulfate pentahydrate (0.936 mL, 0.309 mmol) in ethanol (3.6 mL) and water (0.70 mL) was heated to 80° C. for 1 h. Water was added and the aqueous layer was extracted with EtOAc (×3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and filtered, and the filtrate was evaporated in vacuo to give the crude product. The crude product was purified by preparative TLC on silica gel (0.50 mm thickness) eluting with 30% EtOAc/Hexane to give tert-butyl ((4aR,7aR)-7a-(5-azido-2-fluorophenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-yl)carbamate (100 mg, 0.254 mmol, 36.5% yield) as a white foam. 1H NMR (500 MHz, CHLOROFORM-d) δ 7.30-7.24 (m, 1H), 7.09 (dd, J=10.7, 8.7 Hz, 1H), 7.05-6.93 (m, 1H), 4.23-4.02 (m, 2H), 3.29 (d, J=12.7 Hz, 1H), 2.95 (br. s., 2H), 2.45-2.32 (m, 1H), 2.27-2.15 (m, 1H), 1.50 (s, 9H). MS (M−1): 392.2.

Provenance & Evidence