Reacción #54890

Ecuación de reacción

4-(4-acetyl-8-hydroxytridecyl)-benzoic acid

triethylamine

water

N-t-butyl-5-methylisoxazolium perchlorate

→

N-t-butyl-3-[4-(4-acetyl-8-hydroxytridecyl)benzoyloxy]crotonamide

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe resulting solution is evaporated in vacuo (water aspirator) at 20°-23° C. for 4 hours
2. 2
   Otroproviding a tacky residue which
3. 3
   Otrois triturated with water (150 ml.) at 0°-5° C. for 15 minutes
4. 4
   OtroAfter decanting the aqueous phase
5. 5
   workup.DISSOLUTIONthe oily residue is dissolved in benzene-ether (1:1) (200 ml.)
6. 6
   ExtracciónThe organic extract
7. 7
   Secadois dried over sodium sulfate
8. 8
   Filtraciónfiltered
9. 9
   Otroevaporated in vacuo at 35°-40° C.

Procedimiento

A solution of 4-(4-acetyl-8-hydroxytridecyl)-benzoic acid (3.62 g., 10 millimole), Example 1, Step F, triethylamine (1.74 ml., 12.5 millimole), and distilled water (18 ml., 1.0 mole) in acetonitrile (100 ml.) is treated with N-t-butyl-5-methylisoxazolium perchlorate (3.0 g., 12.5 millimole). The resulting solution is evaporated in vacuo (water aspirator) at 20°-23° C. for 4 hours providing a tacky residue which is triturated with water (150 ml.) at 0°-5° C. for 15 minutes. After decanting the aqueous phase, the oily residue is dissolved in benzene-ether (1:1) (200 ml.). The organic extract is dried over sodium sulfate, filtered, and evaporated in vacuo at 35°-40° C. providing the desired active ester, N-t-butyl-3-[4-(4-acetyl-8-hydroxytridecyl)benzoyloxy]crotonamide, as a pale yellow oil.

Fuente