Acetonitrile → HCID 25169378, compound

Participants

Reaction Steps

To a cooled solution (−30° C.) of (3R,4S,5S,6R)-2-(2-((but-3-ynyloxy)methyl)-4-chloro-5-(4-ethylbenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol (BW) (12 mg, 0.0238 mmol) in 0.5 mL of 1:1 CH2Cl2:CH3CN was added Et3SiH (16 μL, 0.1 mmol) followed by addition of BF3.OEt2 (10 μL, 0.0789 mmol). After stirring for about 4 h, the reaction was quenched with a saturated solution of NaHCO3. The solution was extracted with ethyl acetate and the extracts were washed with brine, followed by drying over Na2SO4. The solution was concentrated and the resulting residue was purified by preparative HPLC to afford 3.5 mg of title product. 1H-NMR (CD3OD, 400 MHz) δ 7.47 (s, 1H), 7.45 (s, 1H), 7.10 (s, 4H), 4.80 (d, J=12.4 Hz, 1H), 4.61 (d, J=12.4 Hz, 1H), 4.49 (d, J=8.8 Hz, 1H), 4.10 (d, J=15.0 Hz, 1H), 4.05 (d, J=15.0 Hz, 1H), 3.88 (dd, J=12.0, 2.0 Hz, 1H), 3.70-3.64 (m, 3H), 3.50 (t, J=8.4 Hz, 1H), 3.46-3.40 (m, 3H), 2.60 (q, J=7.4 Hz, 2H), 2.53-2.49 (m, 2H), 2.30 (t, J=2.6 Hz, 1H), 1.21 (t, J=7.4 Hz, 3H); LC-MS (m/z): 475 [M+H]+, 519 [M+HCO2]−.

Provenance & Evidence