Sodium Hydroxide → HCID 70976494, compound

Participants

Reaction Steps

Methyl 4-((2S,4R)-1-acetyl-2-methyl-4-(pyridin-2-ylamino)-1,2,3,4-tetrahydroquinolin-6-yl)benzoate (for a preparation see Intermediate 22)(700 mg, 1.685 mmol) was dissolved in MeOH (10 ml) and sodium hydroxide solution (2M, 1.68 ml, 3.37 mmol) was added. After 6.5 h a further 2 equivalents of sodium hydroxide (2M, 1.685 ml) was added and reaction mixture stirred overnight. The was concentrated and the residue was diluted with water. Hydrochloric acid (2N, 1 ml) was added forming a precipitate which was isolated by filtration and dried to give 4-((2S,4R)-1-acetyl-2-methyl-4-(pyridin-2-ylamino)-1,2,3,4-tetrahydroquinolin-6-yl)benzoic acid (500 mg, 1.245 mmol, 73.9% yield) as a pinky solid. The aqueous phase was extracted EtOAc (×3) and the combined organic phases were dried over MgSO4 then concentrated in vacuo to give a further batch of 4-((2S,4R)-1-acetyl-2-methyl-4-(pyridin-2-ylamino)-1,2,3,4-tetrahydroquinolin-6-yl)benzoic acid (140 mg, 0.349 mmol, 20.70% yield) as a yellow foam. LCMS (HpH, 2 min), Rt=0.62 min, MH+=402.

Provenance & Evidence