Reaktion #460446

Reaktionsgleichung

17-ethyl-1-hydroxy-12-[2'-(3",4"-dihydroxycyclohexyl)-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

sec-butenyl trichloroacetimidate

Trifluoromethanesulfonic acid

→

17-Ethyl-1-hydroxy-12-[2'-(3"-sec-butenyloxy-4"-hydroxycyclohexyl)-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

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONto mix for 5 minutes
2. 2
   SonstigeAfter 15 minutes the reaction is quenched by the addition of saturated sodiumbicarbonate
3. 3
   Extraktionextracted with ethyl acetate (3×8 ml)
4. 4
   WaschenThe combined organics are washed with brine
5. 5
   Trocknendried over magnesium sulfate
6. 6
   SonstigePurification of the
7. 7
   Einengenconcentrate by preparative TLC on silica gel the title compounds

Vorschrift

To a solution of 17-ethyl-1-hydroxy-12-[2'-(3",4"-dihydroxycyclohexyl)-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 (150 mg in 3 ml 33% methylene chloride in cyclohexane), sec-butenyl trichloroacetimidate (62 μl neat) is added and the reagents allowed to mix for 5 minutes. Trifluoromethanesulfonic acid (2 μl neat) is then added slowly via syringe and the mixture stirred at room temperature. After 15 minutes the reaction is quenched by the addition of saturated sodiumbicarbonate and extracted with ethyl acetate (3×8 ml). The combined organics are washed with brine and dried over magnesium sulfate. Purification of the concentrate by preparative TLC on silica gel the title compounds.

Quelle