Trichloroacetyl isocyanate → HCID 86587924, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2Z,4S,5S,6S,7Z,10S,11R,12R,13S,14S,15Z)-5,11-bis[[(1,1-dimethylethyl) dimethylsilyl]oxy]-13-hydroxy-N,4,6,8,10,12,14-heptamethyl-N-phenyl-2,7,15,17-octadecatetraenamide (110 mg, 0.152 mmol, 1 eq) in CH2Cl2 (2 mL) is treated with trichloroacetyl isocyanate (43 mg, 0.228 mmol, 1.5 eq) at 23° C. (20 minutes). The solution is concentrated, and the residue dissolved in CH3OH (2 mL). To this solution is added K2CO3 (0.1 g) and the mixture is stirred at 23° C. (2 hours). The reaction mixture is concentrated and the residue dissolved in Et2O (5 mL). The organic solution is washed with H2O (1×20 mL) and brine (1×20 mL). The aqueous layer is extracted with Et2O (3×5 mL) and the combined extracts are dried (Na2SO4) and concentrated. Chromatography (SiO2, 30–50% EtOAc-hexanes gradient elution) provided the desired compound (70 mg, 60%).

Provenance & Evidence