Reacción #312603

Ecuación de reacción

hydroxyl-sulfonamide

4-(Benzyloxy)-3-hydroxybutane-1-sulfonamide

Tosyl chloride

water

→

sulfonate

Rendimiento 62.9%

1-(Benzyloxy)-4-sulfamoylbutan-2-yl 4-methylbenzenesulfonate

Rendimiento 62.9%

Disolventes

pyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturamaintaining the internal temperature below 10° C
2. 2
   OtroThe completed reaction
3. 3
   Otroto give an orange solution which
4. 4
   Extracciónwas extracted with iPrOAc/MTBE (1:1, 2×1.5L)
5. 5
   LavadoThe combined organics were washed with brine (2×500 mL), aqueous HCL (2M, 2×500 mL)
6. 6
   SecadoThe organic portion was dried (Na2SO4)
7. 7
   Filtraciónfiltered
8. 8
   Otroevaporated

Procedimiento

A solution of hydroxyl-sulfonamide 5 (77 g, 0.30 mol) in pyridine (730 mL, 9.5 vol) was cooled to <10° C. in a 2 L round bottom flask. Tosyl chloride (56.6 g, 0.30 mol) is added to the solution over 5 minutes maintaining the internal temperature below 10° C. The reaction was allowed to warm to room temperature with stirring overnight. The completed reaction was poured into water (10 vol, 770 mL) to give an orange solution which was extracted with iPrOAc/MTBE (1:1, 2×1.5L). The combined organics were washed with brine (2×500 mL), aqueous HCL (2M, 2×500 mL) then brine (1×500 mL). The organic portion was dried (Na2SO4), filtered and evaporated to give sulfonate 6 as an orange oil (78 g).

Fuente