Triphenylphosphine → HCID 59829670, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 1-(5-{1-azido-2-[8-(benzyloxy)-5-chloroquinolin-7-yl]ethyl}-2-furyl)-N,N-dimethylmethanamine (0.1.451 mmol) in tetrahydrofuran (5 mL) and water (1.5 mL) in a round bottom flask equipped with a reflux condenser was added triphenylphosphine (1.596 mmol, 1.1 eq.) (CAUTION: vigorous gas evolution, do not seal reaction vessel) and the resulting mixture was then warmed to 70° C. and stirred 2 h. The reaction mixture was then allowed to cool to room temperature, diluted with ethyl acetate (50 mL) and was washed with 1N HCl (3×25 mL). The aqueous layers were combined, backextracted with ethyl acetate (25 mL) and then adjusted to pH=12 by addition of 5N NaOH resulting in a precipitate. The aqueous solution was extracted with ethyl acetate (3×50 mL) and the organic layers were combined, dried (MgSO4), filtered and concentrated a yellow oil that was used directly in the ensuing step. MS (ESI) m/z 436.4; HRMS: calcd for C25H26ClN3O2+H+, 436.17863; found (ESI, [M+H]+ Obs'd), 436.1788.

Provenance & Evidence