Glycolic Acid → (S)-N-[3-(4-cyano-2-ethyl-6-methyl-phenoxy)-2-hydroxy-propyl]-2-hydroxy-acetamide

Participants

Reaction Steps

To a solution of (S)-4-(3-amino-2-hydroxypropoxy)-3-ethyl-5-methylbenzonitrile (6.23 g, 26.59 mmol), glycolic acid (2.43 g, 31.9 mmol), HOBt (4.31 g, 31.9 mmol), and EDC hydrochloride (6.12 g, 31.9 mmol) were added. The mixture was stirred at rt for 18 h before it was diluted with sat. aq. NaHCO3 and extracted twice with EA. The combined org. extracts were dried over MgSO4, filtered and concentrated. The crude product was purified by CC with DCM containing 8% of MeOH to give (S)—N-[3-(4-cyano-2-ethyl-6-methyl-phenoxy)-2-hydroxy-propyl]-2-hydroxy-acetamide as a yellow oil (7.03 g). LC-MS: tR=0.74 min; [M+1]+=293.10; 1H NMR (CDCl3): δ 1.25 (t, J=7.5 Hz, 3H), 2.32 (s, 3H), 2.69 (q, J=7.5 Hz, 2H), 3.48-3.56 (m, 3H), 3.70-3.90 (m, 3H), 4.19 (br s, 3H), 7.06 (m, 1H), 7.36 (s, 1H), 7.38 (s, 1H).

Provenance & Evidence