Glycolic Acid → HCID 59272937, compound

Participants

Reaction Steps

A solution of 1-amino-3-{4-[5-(4-isopropoxy-phenyl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-propan-2-ol (277 mg, 0.698 mmol), glycolic acid (80 mg, 1.05 mmol), DIPEA (362 mg, 2.80 mmol) and TBTU (382 mg, 1.19 mmol) in DMF (10 mL) is stirred at rt for 16 h before it is diluted with EA, washed with water, and concentrated. The crude product is purified by chromatography on prep. TLC plates with DCM containing 10% of methanol to give 2-hydroxy-N-(2-hydroxy-3-{4-[5-(4-isopropoxy-phenyl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-propyl)-acetamide (64 mg) as a pale yellow solid, LC-MS: tR=0.94 min, [M+1]+=456.18, 1H NMR (D6-DMSO): δ 1.30 (d, J=5.9 Hz, 6H), 2.31 (s, 6H), 3.16-3.25 (m, 2H), 3.63-3.79 (m, 2H), 3.81 (d, J=5.6 Hz, 2H), 3.86-3.97 (m, 1H), 4.72-4.83 (m, 1H), 5.28 (d, J=5.3 Hz, 1H), 5.54 (t, J=5.9 Hz, 1H), 7.14 (d, J=9.1 Hz, 2H), 7.68 (t, J=5.6 Hz, 1H), 7.73 (s, 2H), 8.08 (d, J=9.1 Hz, 2H).

Provenance & Evidence