Trifluoroacetic acid → HCID 71009133, compound

Participants

Reaction Steps

A solution of {(R)-4-[(1S,2S)-rel-2-(3-chloro-quinolin-8-ylcarbamoyl)-cyclopropyl]-5,5-difluoro-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-yl}-carbamic acid tert-butyl ester (4.7 mg, 9.5 μmol) (intermediate J8.2) in dichloromethane (47 μl) was cooled to 0° C. Trifluoroacetic acid (11.0 mg, 7.4 μl, 95.0 μmol) was added and the solution was left to warm to room temperature. After 7 hours trifluoroacetic acid (33.1 mg, 22.3 μl, 285 μmol) was added again and the mixture stirred at room temperature for another hour. Thereafter, the solvent was removed at reduced pressure. The residue was dissolved in water, then the aqueous layer was basified with a solution of sodium carbonate (2M) and extracted 3 times with dichloromethane. The combined extracts were dried over sodium sulphate and evaporated. The (1S,2S)-rel-2-((R)-2-amino-5,5-difluoro-4-methyl-5,6-dihydro-4H-[1,3]oxazin-4-yl)-cyclopropanecarboxylic acid (3-chloro-quinolin-8-yl)-amide (3.7 mg, 99%) was obtained as a light brown solid. MS (ISP): m/z=395.0 [M+H]+.

Provenance & Evidence