Trimethylsilyl triflate → HCID 86675865, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (S)-1-{(S)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-3-[3-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionyl}-hexahydro-pyridazine-3-carboxylic acid 4-vinyl-pyridin-2-ylmethyl ester (377 mg, 0.52 mmol) in dichloromethane (10 mL) was stirred at 0° C. under nitrogen. Trimethylsilyl trifluoromethanesulfonate (173 mg, 0.14 mL, 0.78 mmol) was added and the reaction mixture was stirred at 0° C. for 1 hour. N,N-Diisopropylethylamine (268 mg, 0.36 mL, 2.08 mmol) was added and the reaction mixture was warmed to room temperature. The solvent was evaporated to afford (S)-1-[(S)-3-[3-(tert-butyl-dimethyl-silanyloxy)-phenyl]-2-((S)-2-formylamino-3-methyl-butyrylamino)-propionyl]-hexahydro-pyridazine-3-carboxylic acid 4-vinyl-pyridin-2-ylmethyl ester (0.52 mmol), which was used crude in the next step. LCMS (m/z) 624 [M+H], Tr=4.30 min.

Provenance & Evidence