Hydrochloric Acid → HCID 178473444, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 1-(4-(6-chloro-2-((3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yloxy)-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-b]pyridin-5-yl)phenyl)piperidin-4-ylcarbamate (44 mg) and KHSO4 (2 M aqueous solution, 40 μL) in formic acid (3 mL) is stirred for 3 hours at 60° C. After diluting with water and cooling to 0° C. NaOH (10 M aqueous solution) is added until the pH >11. Tetrahydrofurane (3 mL) is added and the mixture is stirred for 1 hour at room temperature. Hydrochloric acid (4 N) is added until pH=6. Then the mixture is partitioned between water and ethylacetate and the organic phase is washed with brine and dried (MgSO4). The solvents are evaporated in vacuo and the residue is purified by HPLC on reversed phase to give the title compound. LC (method 1): tR=0.81 min; Mass spectrum (ESI+): m/z=544 [M+H]+.

Provenance & Evidence