Trifluoroacetic acid → HCID 86624976, compound

Participants

Reaction Steps

To a solution of 5′-O—[N-(2-benzyloxybenzoyl)sulfamoyl]-2′-O-tert-butyldimethylsilyl-3′-deoxyadenosine triethylammonium salt (70 mg, 0.092 mmol, 1.0 equiv) in MeOH (10 mL) was added 10% Pd/C (20 mg) and the reaction was stirred under H2 (1 atm) for 8 hours at room temperature. The reaction mixture was filtered through a plug of Celite and the residue was washed with MeOH (4×10 mL). The combined filtrates were concentrated and the crude obtained was treated with 80% aq TFA (2.0 mL) for 8 hours. The reaction was concentrated in vacuo. Purification by flash chromatography (10:90:1 MeOH/EtOAc/Et3N) afforded the title compound (27 mg, 53%) as a viscous oil: Rf 0.3 (1:4 MeOH/EtOAc); [α]20D −10 (c 0.28, MeOH); 1H NMR (600 MHz, CD3OD) δ 1.26 (t, J=7.2 Hz, 9H), 2.05-2.20 (m, 1H), 2.40-2.55 (m, 1H), 3.15 (q, J=7.2 Hz, 6H), 4.32 (dd, J=11.4, 4.2 Hz, 1H), 4.46 (d, J=11.4 Hz, 1H), 4.60-4.80 (m, 2H), 6.00 (s, 1H), 6.70-6.85 (m, 2H), 7.27 (t, J=7.2 Hz, 1H), 7.91 (d, J=7.8 Hz, 1H), 8.12 (s, 1H), 8.47 (s, 1H); 13C NMR (150 MHz, CD3OD) δ 9.3, 34.9, 47.9, 70.7, 76.9, 79.9, 92.9, 117.9, 119.3, 120.3, 120.7, 131.3, 134.3, 140.7, 150.2, 153.7, 157.3, 162.0, 174.9; HRMS (ESI+) calcd for C17H19N6O7S [M+H]+ 451.1030, found 451.1053 (error 5.1 ppm).

Provenance & Evidence