Trifluoroacetic acid → HCID 14186939, compound

Participants

Reaction Steps

To a solution of 13 (4.75 g, 12.16 mmol) in CH2Cl2 (10 mL) is added TFA (10 mL). The solution is stirred for 1 h and then quenched with a saturated solution of NaHCO3 (50 mL). The mixture is extracted with CH2Cl2 (50 mL×2). The combined organic layers are washed with 50 mL portions of sat. NaHCO3, water, and brine. It is then dried over Na2SO4 and concentrated to give pure 14 as a yellow oil (3.07 g, 10.56 mmol, 87%). 1H NMR (400 MHz, CDCl3) δ 0.87 (t, J=6.8 Hz, 3H), 0.91 (d, J=6.8, 3H), 1.65-1.79 (m, 2H), 1.79-1.96 (m, 2H), 1.99-2.17 (m, 1H); 3.27-3.45 (m 1H), 3.46-3.54 (m, 1H), 3.59-3.62 (m, 1H), 4.33-4.38 (m, 1H), 4.46-4.54 (m, 2H), 7.27-7.42 (m, 5H); 13C NMR (100 MHz, CDCl3) δ 16.9, 19.8, 24.4, 27.2, 47.2, 56.6, 58.3, 70.1, 73.1, 127.3, 127.4, 128.2, 138.4, 173.8. HRMS calcd for C17H27N2O2 (MH+): 291.2072. Found (DCI): 291.2088 (Δ=−5.3 ppm).

Provenance & Evidence