Ammonium Hydroxide → HCID 67005159, compound

Participants

Reaction Steps

To a solution of rel-(3R,4R)-4-ethoxy-1-(tetrahydro-2H-pyran-4-yl)pyrrolidin-3-amine (36 mg, 0.168 mmol) in DCM was added {[3-(trifluoromethyl)benzoyl]amino}acetic acid (41.5 mg, 0.168 mmol), HATU (76.7 mg, 0.202 mmol), HOBt (27.2 mg, 0.202 mmol) and DIPEA (0.044 mL, 0.252 mmol) and was stirred at RT overnight. The resulting crude mixture was subjected to flash chromatography (15% MeOH, 1% NH4OH in EtOAc) to afford the title compound (38 mg, 51%) as a white solid. 1H-NMR (CDCl3) δ: 1.17 (t, J=6.9 Hz, 3H), 1.40-1.60 (m, 2H), 1.65-1.82 (m, 2H), 2.22-2.40 (m, 2H), 2.63-2.80 (m, 2H), 3.22-3.51 (m, 4H), 3.63-3.80 (m, 2H), 3.89-4.00 (m, 2H), 4.10-4.20 (m, 2H), 4.24-4.37 (m, 1H), 6.45-6.58 (m, 1H), 7.20-7.30 (m, 1H), 7.56 (t, J=8.1 Hz, 1H), 7.76 (d, J=7.5 Hz, 1H), 7.99 (d, J=7.8 Hz, 1H), 8.08 (s, 1H). MS m/z: 444 (M+1).

Provenance & Evidence