Sodium Cyanide → HCID 67055600, compound

Participants

Reaction Steps

A solution of 4-((2S,3R)-3-[(3S)-3-(acetyloxy)-3-(4-fluorophenyl)propyl]-1-{4-(3-(ethylamino)-3-oxoprop-1-yn-1-yl]phenyl}-4-oxoazetidin-2-yl)phenyl methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosiduronate (11a) (22.0 mg, 0.026 mmol) and sodium cyanide (˜1 mg, 0.020 mmol) in methanol (3 mL) was heated to 45° C. After 18 h, the reaction mixture was concentrated under reduced pressure and dissolved in methanol/water/triethylamine (1:3:1, 2.5 mL). After stirring at room temperature for approximately 1 h, the volatiles were evaporated in vacuo, and the crude residue purified by preparative reversed phase high performance liquid chromatography on YMC Pack Pro C18 phase (gradient elution; 10-60% acetonitrile/water as eluent, 0.1% TFA modifier) to give the title compound (11b) m/z (ES) 663.0 (M+H)+; HRMS (ES) m/z calcd. for C35H36FN2O10 (MH+) 663.2354, found 663.2341.

Provenance & Evidence