Ethyl isocyanate → HCID 178465489, compound

Participants

Reaction Steps

(cis)-4-(4-(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]pyridin-5-yl)phenyl)cyclohexanol (50 mg), 4-dimethylamino-pyridine (DMAP, 1 mg) and triethylamine (30 μL) are dissolved in tetrahydrofurane (1 mL), treated with isocyanatoethane (11 μL) and stirred for 6 hours. Triethylamine (60 μL) and isocyanatoethane (22 μL) are added and the mixture is stirred for 12 hours at 70° C. The mixture is partitioned between ethylacetate and saturated aqueous NH4Cl solution. The organic phase is dried (MgSO4) and concentrated. The residue is used directly in the next step. LC (method 4): tR=1.20 min; Mass spectrum (ESI+): m/z=787 [M+H]+.

Provenance & Evidence