Hydrochloric Acid → HCID 52933865, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-methylethyl((2S,4R)-1-acetyl-6-{3-[({[(1,1-dimethylethyl)oxy]carbonyl}amino)methyl]-1,2,4-oxadiazol-5-yl}-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl)carbamate (for a preparation, see Intermediate 62) (100 mg, 0.205 mmol) in 1,4-dioxane (0.5 mL) at room temperature was added HCl (4N in 1,4-dioxane, 2 mL, 8 mmol) and the resulting mixture was stirred at this temperature for 3 h than at 4° C. for 16 h before being warmed to room temperature. The residue was triturated with Et2O then purified using MDAP (modifier: ammonium bicarbonate). The residue obtained was dissolved in 1,4-dioxane (2 mL) and treated with HCl (4N in dioxane, 1 mL). The resulting mixture was concentrated in vacuo and the residue triturated with Et2O to give 1-methylethyl {(2S,4R)-1-acetyl-6-[3-(aminomethyl)-1,2,4-oxadiazol-5-yl]-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl}carbamate hydrochloride (9 mg, 0.021 mmol, 10.35% yield).

Provenance & Evidence