Glycolic Acid → N-((2S)-3-{4-[3-(2-Cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-5-yl]-2-ethyl-6-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide

Participants

Reaction Steps

To a solution of (2S)-1-amino-3-{4-[3-(2-cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-5-yl]-2-ethyl-6-methyl-phenoxy}-propan-2-ol (100 mg, 220 μmol), glycolic acid (22 mg, 289 μmol) and DIPEA (86 mg, 666 μmol) in DMF (3 mL), TBTU (93 mg, 289 μmol) is added. The mixture is stirred at rt for 1 h before it is diluted with EA (50 mL) and washed with sat. aq. NaHCO3 solution (20 mL) followed by brine (20 mL). The org. extract is dried over MgSO4, filtered and concentrated. The crude product is purified by prep. HPLC to give the title compound (65 mg) as an almost colourless oil; LC-MS**: tR=0.84 min, [M+H]+=511.03; 1H NMR (CDCL3): δ1.33 (t, J=7.5 Hz, 3H), 1.68-1.79 (m, 2H), 1.82-1.95 (m, 4H), 2.05-2.15 (m, 2H), 2.41 (s, 3H), 2.76 (q, J=7.5 Hz, 2H), 3.18-3.28 (m, 1H), 3.49-3.59 (m, 1H), 3.75-3.95 (m, 3H), 4.01 (s, 3H), 4.18-4.26 (m, 3H), 7.08 (t, J=4.3 Hz, 1H), 7.49 (s, 1H), 7.91 (s, 1H), 7.93 (s, 1H).

Provenance & Evidence