Reacción #8235

Ecuación de reacción

methyl 4-{[{2-[2-({4-[2-(4-{[tert-butyl(dimethyl)-silyl]oxy}phenyl)ethyl]benzyl}oxy)phenyl]ethyl}(5-ethoxy-5-oxopentyl)amino]-methyl}benzoate

tetrabutylammonium fluoride

→

4-[((4-carboxybutyl)[2-[2-([4-[2-(4-hydroxyphenyl)ethyl]benzyl]oxy)phenyl]-ethyl]amino)methyl]benzoic acid

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solvents are evaporated under reduced pressure
2. 2
   workup.DISSOLUTIONThe residue is dissolved in 2 ml of methanol
3. 3
   workup.ADDITION0.05 ml of aqueous sodium hydroxide solution, 45%, and 0.2 ml of dichloromethane are added
4. 4
   workup.STIRRINGthe solution is stirred at RT for 8 hours
5. 5
   ConcentraciónThe mixture is concentrated
6. 6
   workup.ADDITIONwater is added
7. 7
   FiltraciónThe solid is filtered off
8. 8
   Otrodried

Procedimiento

27 mg (0.037 mmol) of methyl 4-{[{2-[2-({4-[2-(4-{[tert-butyl(dimethyl)-silyl]oxy}phenyl)ethyl]benzyl}oxy)phenyl]ethyl}(5-ethoxy-5-oxopentyl)amino]-methyl}benzoate from XXI are dissolved in 10 ml of THF. 0.03 ml of tetrabutylammonium fluoride (IM solution in THF) are added, and the solution is stirred at RT for 1 hour. The solvents are evaporated under reduced pressure. The residue is dissolved in 2 ml of methanol. 0.05 ml of aqueous sodium hydroxide solution, 45%, and 0.2 ml of dichloromethane are added, and the solution is stirred at RT for 8 hours. The mixture is concentrated, water is added and the solution is acidified using sulphuric acid. The solid is filtered off and dried.

Fuente