p-Toluenesulfonic acid monohydrate → HCID 54077611, compound

Participants

Reaction Steps

To a stirred solution of 17-ethyl-1,14-dihydroxy-12-[2'-(4"-(1-methyl-3-(2-t-butyldimethylsilyloxyethyl)indol-5-yl)oxy-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 (200 mg.) in CH2Cl2 (6 mL.) and CH3OH (6 mL.) was added p-toluenesulfonic acid monohydrate (30 mg.). The reaction mixture was allowed to stir 3 hours. The reaction was quenched with saturated aqueous NaHCO3 and extracted 4× with CH2Cl2. The organic extracts were combined, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The product was purified by preparative TLC on silica gel (1:1 hexanes/acetone) and again (7% CH3OH/CH2Cl2) giving -(4"-(1-methyl-3-(2-hydroxyethyl)indol-5-yl)oxy-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.

Provenance & Evidence