反応 #312603

反応方程式

hydroxyl-sulfonamide

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

Tosyl chloride

water

→

sulfonate

収率 62.9%

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

収率 62.9%

溶媒

pyridine

反応条件

後処理

1. 1
   温度maintaining the internal temperature below 10° C
2. 2
   その他The completed reaction
3. 3
   その他to give an orange solution which
4. 4
   抽出was extracted with iPrOAc/MTBE (1:1, 2×1.5L)
5. 5
   洗浄The combined organics were washed with brine (2×500 mL), aqueous HCL (2M, 2×500 mL)
6. 6
   乾燥The organic portion was dried (Na2SO4)
7. 7
   ろ過filtered
8. 8
   その他evaporated

実験手順

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).

出典