Hydrochloric Acid → HCID 86669272, compound

Participants

Reaction Steps

To a solution of 1-methylethyl((2S,4R)-1-acetyl-6-{5-[({[(1,1-dimethylethyl)oxy]carbonyl}amino)methyl]-1,2,4-oxadiazol-3-yl}-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl)carbamate (for a preparation, see Intermediate 60) (132 mg, 0.271 mmol) in 1,4-dioxane (2 mL) at room temperature was added HCl (4N in 1,4-dioxane, 2 mL, 8.00 mmol) and the resulting mixture was stirred at this temperature for 5 h then left standing at 4° C. for 16 h. The mixture was warmed to room temperature and most of the solvent was removed in vacuo. The residue was loaded on a 2 G SCX cartridge and eluted with MeOH then with a 2N NH3 solution in MeOH. The ammonia fractions were collected and concentrated in vacuo, The residue was dissolved in 1,4-dioxane (3 mL) and the solution was treated with 0.5 ml of HCl (4N in 1,4-dioxane) then concentrated in vacuo. Trituration of the residue with Et2O gave 1-methylethyl {(2S,4R)-1-acetyl-6-[5-(aminomethyl)-1,2,4-oxadiazol-3-yl]-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl}carbamate hydrochloride (71 mg, 0.167 mmol, 61.9% yield) as a pale red solid.

Provenance & Evidence