Reaction #312603

Reaction equation

hydroxyl-sulfonamide

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

Tosyl chloride

water

→

sulfonate

Yield 62.9%

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

Yield 62.9%

Solvents

pyridine

Conditions

Workup

1. 1
   Temperaturemaintaining the internal temperature below 10° C
2. 2
   OtherThe completed reaction
3. 3
   Otherto give an orange solution which
4. 4
   Extractionwas extracted with iPrOAc/MTBE (1:1, 2×1.5L)
5. 5
   WashThe combined organics were washed with brine (2×500 mL), aqueous HCL (2M, 2×500 mL)
6. 6
   DryingThe organic portion was dried (Na2SO4)
7. 7
   Filtrationfiltered
8. 8
   Otherevaporated

Procedure

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).

Source