Reacción #6401

Ecuación de reacción

17-ethyl-1,14-dihydroxy-12-[2'-(4"-(3'"-dioxolanylphenyloxy)-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

p-toluensulfonic acid

→

title compound

Rendimiento 31.5%

17-Ethyl-1,14-dihydroxy-12-[2'-(4"-(3'"-formylphenyloxy)-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

Rendimiento 31.5%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAfter 20 minutes the reaction was quenched by the addition of 2 ml saturated sodium bicarbonate
2. 2
   Extracciónextracted with methylene chloride
3. 3
   Lavadowashed with brine
4. 4
   SecadoThe combined organics were dried over magnesium sulfate
5. 5
   Otrothe concentrate purified by preparative tlc on silica gel (2:1, hexane/acetone)

Procedimiento

To a solution of 17-ethyl-1,14-dihydroxy-12-[2'-(4"-(3'"-dioxolanylphenyloxy)-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 (20 mg in 1 ml methylene chloride) was added 1 ml of a 2.2% solution of p-toluensulfonic acid in methanol and the mixture stirred at room temperature. After 20 minutes the reaction was quenched by the addition of 2 ml saturated sodium bicarbonate, extracted with methylene chloride and washed with brine. The combined organics were dried over magnesium sulfate and the concentrate purified by preparative tlc on silica gel (2:1, hexane/acetone) to give the title compound (6 mg).

Fuente