1-Adamantanecarboxylic acid → HCID 178472637, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the product from Example 77A (0.75 g, 2.8 mmol) and 1-adamantanecarboxylic acid (0.56 g, 3.1 mmol) in 14 mL of THF at 0° C. was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (1.2 g, 3.1 mmol) and diisopropylethylamine (1.1 mL, 6.2 mmol). The mixture was heated to 65° C. for 2.5 hours, cooled to ambient temperature and then diluted with ethyl acetate. The mixture was washed twice with water, saturated aqueous sodium bicarbonate, and brine. The organic extract was dried over magnesium sulfate, and concentrated under reduced pressure. Purification by column chromatography (SiO2, 30-50% ethyl acetate/hexanes gradient) afforded 0.79 g (81%) of the title compound. 1H NMR (CDCl3, 300 MHz) δ ppm 1.29 (t, J=7.1 Hz, 3H), 1.69-1.76 (m, 6H), 1.93-1.94 (m, 6H), 1.99-2.04 (m, 3H), 4.25 (q, J=7.3 Hz, 2H), 4.84 (s, 2H), 6.60 (d, J=5.1 Hz, 1H), 6.93 (d, J=4.7 Hz, 1H); MS (DCI/NH3) m/z 349 (M+H)+. Anal. Calculated for C18H24N2O3S: C, 62.04; H, 6.94; N, 8.04. Found: C, 62.24; H, 7.08; N, 8.04.

Provenance & Evidence