2,2,2-Trifluoroethyl trifluoromethanesulfonate → HCID 59718683, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 200 mg of ((S)-7,8-difluoro-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl ester in 7 ml of tetrahydrofurane was cooled to −78° C. under an argon atmosphere. Thereafter, the solution was treated with 0.62 ml of lithium bis(trimethylsilyl)amide (1 M solution in tetrahydrofurane), stirred for 30 min at −78° C., then warmed to room temperature before 0.13 ml of 2,2,2-trifluoroethyl trifluoromethanesulphonate were added to the reaction mixture. After stirring overnight in a sealed flask, another 0.05 ml of 2,2,2-trifluoroethyl trifluoromethanesulphonate were added and stirring continued for 18 hours. For the working-up, the reaction mixture was evaporated under reduced pressure and the residue was directly submitted to chromatography on a Si—NH2 phase using a gradient of heptane/ethyl acetate=100/0 to 60/30 as the eluent. There were obtained 193 mg (77% of theory) of the title compound as a white foam; MS 418 (M+Na)+.

Provenance & Evidence