Tetrahydrofuran → HCID 42635717, compound

Participants

Reaction Conditions

Reaction Steps

4.30 mmol of NaOH are added to a solution of 1.05 mmol of (3R,4R,5S)-4-(4-methoxycarbonyl-phenyl)-3-[4-(3-methoxy-propyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-5-triisopropylsilanyloxymethyl-piperidine-1-carboxylic acid tert-butyl ester in 10 ml of THF and 10 ml of H2O. The resulting reaction mixture is stirred at 90° C. for 16 h and then cooled to RT. After dilution with H2O and acidification (pH 3) with 4N aqueous HCl, the mixture is extracted with TBME (2×)—the combined organic phases are washed with brine, dried over Na2SO4 and concentrated by evaporation. The crude title compound is obtained as a viscous brown oil. Rf=0.24 (EtOAc/heptane 2:1+a drop of formic acid); Rt=6.71 (gradient I).

Provenance & Evidence