Trifluoromethanesulfonic anhydride → HCID 70169699, compound

Participants

Reaction Steps

To a stirred solution of (S)-N-[1-(tert-butoxycarbonyl)pyrrolidin-3-yl]-N-{2-[1-(triphenylmethyl)-1H-imidazol-4-yl]ethyl}carbamic acid triisopropylsilyl ester, as described above in Step F, (519 mg, 0.715 mmol) and 4-cyano-3-fluoro-benzyl alcohol, as described in Example 31, Step H, (108 mg, 0.715 mmol) in CH2Cl2 (7 mL) was added N,N-diisopropylethylamine (0.311 mL, 1.78 mmol), followed by dropwise addition of trifluoromethanesulfonic anhydride (0.120 mL, 0.715 mmol). The reaction mixture was allowed to warm slowly to ambient temperature and was stirred for 18 hours, then concentrated in vacuo. The residue was dissolved in MeOH (10 mL) and the resulting solution was heated to 40° C. for 2 hours. The solvent was removed in vacuo and the residue was chromatographed on silica gel, eluting with a gradient of CH2Cl2—1% to 4% MeOH—0.1% to 0.4% NH4OH, to yield the above-titled compound.

Provenance & Evidence