Trifluoroacetic acid → N-(4-amino-5-methyl-3-oxohexyl)-2,2-dichloro-N-(2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)pyridin-4-yl)acetamide

Participants

Reaction Conditions

Reaction Steps

Trifluoroacetic acid (1 mL) was added to a solution of tert-butyl 6-(2,2-dichloro-N-(2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)pyridin-4-yl)acetamido)-2-methyl-4-oxohexan-3-ylcarbamate (185 mg, 0.29 mmol) in methylene chloride (2 mL) at 0° C. The resulting mixture was allowed to stir at 0° C. for 2 hours, then concentrated under reduced pressure. The residue was dissolved in methylene chloride (2 mL) and concentrated under reduced pressure, twice more. Then lyophilized to produce N-(4-amino-5-methyl-3-oxohexyl)-2,2-dichloro-N-(2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)pyridin-4-yl)acetamide (Cpd. No. 3, lot 2, 150 mg) as a light orange solid. 1H NMR (CD3OD): 8.90 (d, 1H), 8.28 (s, 1H), 7.80-7.75 (m, 1H), 7.65-7.55 (m, 3H), 7.38 (s, 1H), 6.62 (s, 1H), 4.38-4.11 (m, 3H), 3.19-3.08 (m, 2H), 2.55-2.41 (m, 1H), 1.15 (d, 3H), 0.90 ppm (d, 3H). MW=544 confirmed by LC-MS, tr=10.55 min (Method Y) MH+=542-546.

Provenance & Evidence