Glycolic Acid → HCID 24752895, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (RS)-1-amino-3-{4-[5-(5-chloro-6-isopropoxy-pyridin-3-yl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-propan-2-ol (313 mg, 0.6 mmol) in DCM (10 mL), glycolic acid (95 mg, 1.25 mmol) and Hünig's base (233 mg, 1.8 mmol) are added. The mixture is cooled to 0° C. and TBTU (236 mg, 0.74 mmol) is added. The mixture is stirred at 0° C. for 1 h, then at rt for 16 h before it is diluted with EA (250 mL), washed with 1N aq. NaOH solution (3×25 mL), 1N aq. KHSO4 (25 mL) and brine (25 mL), dried over Na2SO4, filtered and concentrated. The crude product is purified by prep. HPLC to give N—((RS)-3-{4-[5-(5-chloro-6-isopropoxy-pyridin-3-yl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide (42 mg) as a white powder; LC-MS: tR=1.06 min; [M+1]+=491.48; 1H NMR (CD3OD) δ 1.45 (d, J=6.3 Hz, 6H), 2.38 (s, 6H), 3.47 (dd, J=13.6, 7.3 Hz, 1H), 3.66 (dd, J=13.6, 4.5 Hz, 1H), 3.87 (m, 2H), 4.04 (s, 2H), 4.14 (m, 1H), 5.52 (m, 1H), 7.78 (s, 2H), 8.43 (s, 1H), 8.85 (s, 1H)

Provenance & Evidence