Water → HCID 178455378, compound

Participants

Reaction Conditions

Reaction Steps

5-(4-((trans)-4-Azidocyclohexyl)phenyl)-2-((3R,3aR,6R,6aS)-6-(tert-butyldimethyl-silyloxy)hexahydrofuro[3,2-b]furan-3-yloxy)-6-chloro-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-b]pyridine (130 mg) is dissolved in tetrahydrofurane (1 mL), treated with triphenylphosphine (57 mg) and stirred for 24 hours at 40° C. Then water (220 μL) is added and the mixture is stirred for 12 hours at 80° C. The mixture is partitioned between ethylacetate and saturated aqueous NH4Cl solution. The organic phase is dried (MgSO4) and concentrated. The residue is purified by HPLC on reversed phase to give the product, which is partitioned between 1 M aqueous NaOH solution and ethylacetate. The organic phase is washed with brine and dried (MgSO4). The residue is concentrated to give the title compound. LC (method 1): tR=1.24 min; Mass spectrum (ESI+): m/z=715 [M+H]+.

Provenance & Evidence