Sodium Hydroxide → {4-[(2S,4R)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]-1H-1,2,3-triazol-1-yl}acetic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl {4-[(2S,4R)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]-1H-1,2,3-triazol-1-yl}acetate (for a preparation, see Intermediate 75) (250 mg, 0.582 mmol) in methanol (5 mL) was added a 2M NaOH aqueous solution (0.873 mL, 1.746 mmol). The reaction mixture was stirred at 50° C. for 1 hour, then cooled to room temperature and concentrated in vacuo. The residue was partitioned between AcOEt and a 2M NaOH aqueous solution. The layers were separated and the organic phase was further extracted with a 2M NaOH aqueous solution. The combined aqueous layers were acidified to pH=3 using a 2M HCl aqueous solution. then extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over a Na2SO4 cartridge and concentrated in vacuo to give {4-[(2S,4R)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]-1H-1,2,3-triazol-1-yl}acetic acid (245 mg, 0.566 mmol, 97%) as a white solid.

Provenance & Evidence