Hydrochloric Acid → 1-methylethyl((2S,4R)-1-acetyl-6-{4-[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]phenyl}-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl)carbamate hydrochloride

Participants

Reaction Steps

Trifluoroacetic acid (TFA) (3 mL) was added to a solution of 1-methylethyl((2S,4R)-1-acetyl-6-{4-[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]phenyl}-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl)carbamate (for a preparation see Intermediate 87) (50 mg, 0.098 mmol) in dichloromethane (DCM) (3.00 mL) and the resulting mixture was stirred at room temperature under nitrogen for 3 h then concentrated in vacuo. The residue obtained was co-evaporated with toluene then purified using a SCX column (5 g, elution 5 column volume (CV) methanol, then 5 CV 2M NH3 in methanol). The ammonia fractions were collected and concentrated in vacuo to give a residue which was treated with HCl (1.0 M in Et2O, 2 mL, 2 mmol). The resulting mixture was concentrated in vacuo to give 1-methylethyl((2S,4R)-1-acetyl-6-{4-[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]phenyl}-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl)carbamate hydrochloride (50 mg, 0.098 mmol, 80%) as a white solid.

Provenance & Evidence