Acetic Acid → HCID 70976510, compound

Participants

Reaction Steps

A solution of methyl 4-((2S,4R)-1-acetyl-4-((tert-butoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate (for a preparation see Intermediate 30)(5.23 g, 11.93 mmol) in MeOH (80 mL) was treated with aqueous lithium hydroxide (1M, 17.89 mL, 17.89 mmol) and the resulting mixture, which became a suspension after 5 min was stirred. After 24 h, lithium hydroxide (17.89 mL, 17.89 mmol) was added and the mixture (which by then was a solution) was stirred at 50° C. for 3 h. The mixture was cooled to room temperature, most of the MeOH was evaporated in vacuo and the residue treated with acetic acid (2.73 mL, 47.7 mmol). After 5 min, a precipitate formed, was isolated by filtration, washed with water and dried at 45° C. under vacuum for 16 h to give 4-((2S,4R)-1-acetyl-4-((tert-butoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoic acid (4.88 g, 11.50 mmol, 96% yield) as a white solid. LCMS (HpH, 2 min), Rt=0.70 min, MH+=425.

Provenance & Evidence