Tetrahydrofuran → HCID 67413236, compound

Participants

Reaction Steps

To a solution of {(R)-1-[6-(4-Cyclopentyl-cyclohexyloxy)-5-trifluoromethylnaphthalen-2-yl]-2-hydroxy-1-methyl-ethyl}-carbamic acid tert-butyl ester (11 mg, 0.000020 mol) and 1H-tetrazole (14 mg, 0.00020 mol) in tetrahydrofuran (3 mL, 0.04 mol) was added di-tert-butyl N,N-Diethylphosphoramidite (28 μL, 0.00010 mol) at RT. The reaction was then quenched with 10% NaS2O3 in saturated sodium bicarbonate, extracted with EtOAc, washed with saturated sodium chloride and then dried with Na2SO4. The drying agent was filtered and the organic layer was concentrated under vacuum, yielding the crude product. The crude was taken up in DCM and purified using silica gel chromatography (24 g column), 0-100% ethyl acetate in hexanes) to give 12 mg of the desired compound as a white solid (77%). ESI-MS: 728 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ=8.18-8.08 (m, 1 H), 7.92 (d, J=9.0 Hz, 1 H), 7.63-7.42 (m, 2 H), 7.22 (dd, J=5.0, 9.0 Hz, 1 H), 4.32-4.11 (m, 1 H), 3.98-3.80 (m, 2 H), 2.18-1.98 (m, 2 H), 1.92-0.71 (m, 46 H)

Provenance & Evidence