Diethyl Ether → HCID 86596154, compound

Participants

Reaction Steps

(2-{4-[2-(Cyanomethylcarbamoyl)-cyclohexylmethylsulfanyl]-2-fluorophenylsulfanyl}-ethyl)-carbamic acid tert-butyl ester was dissolved in tetrahydrofuran (3 mL) and methanesulfonic acid (0.428 g, 6.6 mmol) was added. The reaction mixture was stirred at room temperature overnight, whereupon ether (100 mL) was added. The supernatant was discarded. The residue was triturated three times with ether (50 mL) then 10% tetrahydrofuran/ether, resulting in a white solid, N-cyanomethyl 2-[4-(2-aminoethylsulfanyl)-3-fluoro-phenylsulfanylmethyl]-cyclohexanecarboxamide mesylate, which was isolated by filtration in near quantitative mass recovery, with a small amount of t-butyl amide present as an inseparable impurity, resulting from addition of tert-butanol across the nitrile group under the acidic Boc-cleavage conditions. MS [ESI, (M+H)+] m/z=412 amu.

Provenance & Evidence