Reacción #1478590

Ecuación de reacción

2-aminoacetophenone

D-biotin

N-methylmorpholine

isobutyl chloroformate

→

crude product 1c

Rendimiento 72.0%

Biotin ortho-acetophenone

Rendimiento 72.0%

Disolventes

DMF

ether

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe solution is maintained
2. 2
   workup.STIRRINGstirred at room temperature for 3 h 30 min
3. 3
   Otroevaporated to dryness
4. 4
   OtroThe precipitate obtained
5. 5
   Filtraciónis filtered
6. 6
   Lavadowashed with water
7. 7
   OtroThe precipitate obtained
8. 8
   Filtraciónis filtered
9. 9
   Lavadowashed with water
10. 10
    OtroRecrystallization
11. 11
    workup.DISSOLUTIONby dissolving the product in MeOH in the hot state
12. 12
    Otroreprecipitating by addition of water
13. 13
    FiltraciónThe precipitate is filtered
14. 14
    Lavadowashed with water

Procedimiento

The D-biotin (1 g, 4.1 mmol) is solubilized in 45 ml of anhydrous DMF in the hot state. The mixture is cooled to 0° C. under argon, and then N-methylmorpholine (590 μl, 5.33 mmol) and isobutyl chloroformate (840 μl, 6.60 mmol) are successively added. The mixture is kept stirred for 30 min, and then 2-aminoacetophenone (824 mg, 6.10 mmol) is added. The solution is maintained stirred at room temperature for 3 h 30 min, and then evaporated to dryness. The residue is taken up in 50 ml of water. The precipitate obtained is filtered, washed with water and then with 50 ml of MeOH in the hot state. The precipitate obtained is filtered and washed with water. Recrystallization is carried out by dissolving the product in MeOH in the hot state and reprecipitating by addition of water. The precipitate is filtered, washed with water, and then with ether to give 1.1 g (2.95 mmol, 72%) of crude product 1c.

Fuente