Di-tert-butyl dicarbonate → HCID 24757051, compound

Participants

Reaction Steps

To a solution of (R)-1-{-1-[2-({[3,5-bis(trifluoromethyl)benzyl](2-methyl-2H-tetrazol-5-yl)amino}methyl)-4-(trifluoromethyl)phenyl]-2-methylpropyl}piperidine-4-carboxylic acid (0.510 g, 0.76 mMol) in THF (5 mL) was added ditert-butyl dicarbonate (0.21 g, 0.99 mMol) and ammonium carbonate (0.078 g, 0.99 mMol) at 0° C. To this solution was added pyridine (0.037 mL) and the mixture was stirred overnight at room temperature. The reaction mixture was poured into saturated sodium bicarbonate and extracted with ethyl acetate. The extracts were washed with saturated solution of sodium hydrogen sulfate and brine. The organic extract was dried and purified by flash chromatography to afford the product (0.314 g., 65%) 1HNMR (400 MHz. CDCl3) δ 7.80 (s, 1H), 7.60 (d, 2H), 7.50 (m, 1H), (7.20, m, 1H), 7.25 (d, 1H), 5.20 (m, 2H), 4.90 (d, 1H), 4.70 (dd, 2H), 4.50 (dd, 1H, 4.20 (s, 3H), 3.60 (d, 1H), 3.0 (m, 1H), 2.80 (m, 1H), 2.20 (m, 1H), 1.80 (m, 2H), 1.70 (m, 4H), 0.8 (d, 3H), 0.6 (d, 3H). MS (ES+) Calc 665.60, Found 666.7 (M+1)

Provenance & Evidence