Methanol → 1-isobutyl-3-[2-[4-[3-[4-[[4-methyl-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]indol-3-yl]methyl]phenoxy]propyl]-4,9-diazaspiro[5.5]undecan-9-yl]-2-oxo-ethyl]urea

Participants

Reaction Steps

Cool a mixture of [(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-[3-[[4-[3-[9-[2-(isobutylcarbamoylamino)acetyl]-4,9-diazaspiro[5.5]undecan-4-yl]propoxy]phenyl]methyl]-4-methyl-indol-1-yl]tetrahydropyran-2-yl]methyl acetate (74.28 mmoles; 68.20 g) and methanol (341.00 mL) in an ice-bath. Add sodium methoxide (111.43 mmoles; 6.02 g). Stir the mixture for 10 minutes. Pour the mixture into water (3.5 L), then filter the mixture. Wash the solid with water, dry on the sinter, and further dry in a vacuum oven at 60° C. to give the title compound (49.8 g, 89% yield) mass spectrum (m/z): 750.6 (M+1).

Provenance & Evidence