Triethylamine → HCID 28165569, compound

Participants

Reaction Steps

To a mixture of (R)-2-(tert-butoxycarbonylamino)-3-methylbutanoic acid (1.0 g, 4.60 mmol), HATU (2.1 g, 5.52 mmol) and pyrrolidine (0.812 mL, 9.21 mmol) in DCM (30 mL) was added Et3N (1.28 mL, 9.21 mmol). The reaction mixture was stirred at room temperature for 5 h and then washed with saturated aqueous NaHCO3 and brine. The organics were dried over MgSO4 and concentrated. Purification by silica column chromatography (MeOH/DCM, 0-10%) afforded the title compound as a light yellow oil (1.18 g, 95%). 1H NMR (400 MHz, CDCl3) δ 0.95 (d, J=18.95 Hz, 3 H) 0.95 (d, J=5.31 Hz, 3 H) 1.30-1.53 (m, 9 H) 1.77-2.07 (m, 5 H) 3.33-3.59 (m, 3 H) 3.59-3.80 (m, 1 H) 4.25 (dd, J=9.35, 6.57 Hz, 1 H) 5.30 (d, J=9.09 Hz, 1 H).

Provenance & Evidence