Water → HCID 178455377, compound

Participants

Reaction Conditions

Reaction Steps

5-(4-((cis)-4-Azidocyclohexyl)phenyl)-2-((3R,3aR,6R,6aS)-6-(tert-butyldimethylsilyloxy)hexahydrofuro[3,2-b]furan-3-yloxy)-6-chloro-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-b]pyridine (210 mg) is dissolved in tetrahydrofurane (1 mL) treated with triphenylphosphine (90 mg) and stirred for 4 hours at room temperature and for 12 hours at 40° C. Water (220 μL) is added and the mixture is stirred for further 12 hours at 80° C. Then the mixture is partitioned between hydrochloric acid (1 M) and diethylether. The organic phase is washed with aqueous NaOH solution (1 M), dried (MgSO4) and concentrated. The residue is chromatographed over aluminium oxide (ethyl acetate/methanol 100:0→0:100) to give the title compound. LC (method 4): tR=0.61 min; Mass spectrum (ESI+): m/z=715 [M+H]+.

Provenance & Evidence