Acetic Acid → HCID 67774058, compound

Participants

Reaction Steps

NaOH (2.35 ml, 8.93 mmol) was added to (S)-2-(4-chloro-N-methylbenzamido)-3-methylbutyl 4-chlorobenzoate (Compound C2.1) (3.2 g, 8.12 mmol) in MeOH. The resultant mixture was stirred at rt for 20 min. Additional NaOH (1.07 ml, 4.06 mmol) was added and the stirring continued for 1 h. To the mixture was water (5 mol) added and the resultant mixture was stirred for 2 h. The mixture was neutralized by the addition of acetic acid. The solvent was removed and DCM (50 mL) was added. The organic phase was washed with NaHCO3 (saturated, 3×50 mL), filtered through a phase separator and concentrated under reduced pressure to give the title compound (1.47 g, 71%). The obtained crude product was used without further purification. Mixture of rotamers: (600 MHz, CD3OD) δ 0.78-0.85, 0.95-0.99, 1.02-1.07, 1.78-1.86, 1.90-1.98, 2.84, 2.95, 3.35-3.40, 3.59-3.66, 3.68-3.77, 3.83-3.88, 4.28-4.34, 7.39-7.48. Total no of protons: 17. LCMS (M+H)+: 256.

Provenance & Evidence