N,N-Diethylethanamine trihydrofluoride → HCID 86628924, compound

Participants

Reaction Conditions

Reaction Steps

Following the general procedure for the cleavage of silyl ethers with triethylamine trihydrofluoride of Description 20, a mixture of (5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl (2R)-4-{[(3-acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(1,1,2,22-tetramethyl-1-silapropoxy)butanoate (48a) (100 mg, 0.18 mmol) and triethylamine trihydrofluoride (Et3N.3HF) 150 μL (149 mg, 0.93 mmol) in 2 mL of tetrahydrofuran (THF) was stirred overnight at ca. 50-60° C. (oil bath). After work-up and further purification by mass-guided preparative HPLC and lyophilization of the solvents, 6.2 mg (8.1% yield) of the title compound (48) was obtained as a colorless, viscous oil. 1H NMR (400 MHz, CDCl3): δ=1.03 (s, 3H), 1.11 (s, 3H), 2.01 (s, 3H), 2.04-2.11 (m, 2H), 2.22 (s, 3H), 3.10-3.23 (m, 2H), 3.31-3.46 (m, 2H), 4.00 (d, J=9.2 Hz, 1H), 4.07-4.10 (m, 2H), 4.93 (d, J=14.0 Hz, 1H), 5.03 (d, J=13.6 Hz, 1H), 5.86-5.88 (br. m, 1H) ppm. MS (ESI) m/z 424.01 (M+H)+, 446.01 (M+Na)+. The analytical data was consistent with the proposed structure.

Provenance & Evidence