Acetic Acid → HCID 68185441, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-methylethyl {(2S,4R)-1-acetyl-6-[acetyl(2-oxopropyl)amino]-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl}carbamate (for a preparation see Intermediate 110) (130 mg, 0.322 mmol), ammonium acetate (124 mg, 1.611 mmol) and acetic acid (2 mL, 34.9 mmol) was stirred at 120° C. under nitrogen for 24 h then cooled to room temperature and basified with NaOH (2N in water). The mixture was then partitioned between AcOEt (10 mL) and water (5 mL) and the phases were separated. The organic layer was washed with a saturated NaHCO3 aqueous solution, dried over Na2SO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (gradient: 100% AcOEt then 0 to 10% MeOH in DCM) gave 1-methylethyl[(2S,4R)-1-acetyl-6-(2,4-dimethyl-1H-imidazol-1-yl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (28 mg, 0.062 mmol, 19%) as a yellow gum.

Provenance & Evidence