Hydrochloric Acid → HCID 86587923, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2Z,4S,5S,6S,7Z,10S,11R,12R,13S,14S,15Z)-13-[(aminocarbonyl)oxy]-5,11-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-N,4,6,8,10,12,14-heptamethyl-N-phenyl-2,7,15,17-octadecatetraenamide (70 mg, 0.091 mmol, 1 eq) in MeOH (10 mL) is added a MeOH solution of HCl (15.5 mL, 15 mL MeOH+0.5 mL 12N HCl). The resulting solution is stirred at 23° C. (36 hours). The pH is adjusted to 8 by the addition of solid NaHCO3 at 0° C. The solution was dried in vacuo, the residue was dissolved in CH2Cl2 (10 mL) and filter through Celite. HPLC purification provided the desired compound (15.5 mg, 32%) as a white solid: [α]25D=+225.738° (c 0.25, CH2Cl2); HRMS ESI m/z 541.3588 (M+H+, C32H50O5N2 requires 541.3641).

Provenance & Evidence