Tacrolimus-13C,D2 → HCID 57194283, compound

Participants

Reaction Steps

To a cooled solution (0° C.) of 17-allyl-1,14-dihydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-1'-methylvinyl]23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]-octacos-18-ene-2,3,10,16-tetraone (120 mg) in dry methylene chloride (15 ml) is added 2,6-lutidine (64.3 mg) followed by triisopropylsilyl trifluoromethanesulfonate (184 mg). Reaction temperature is raised to r.t. and stirred overnight under nitrogen atmosphere. The reaction is quenched with 10 ml of water and extracted with ethyl acetate. Organic layer is washed (water, sat'd NaHCO3, sat'd NaCl) and dried (anhydrous MgSO4). Removal of solvent followed by chromatography on silica gel (70% hexane/ethyl acetate) gives the title compound.

Provenance & Evidence