Reaction #317792

Reaction equation

3-aminopropylsulfinic acid

sodium bicarbonate

compound ( 17 )

[(1-Isobutanoyloxyethoxy)carbonyloxy] Succinimide

→

title compound ( 31 )

3-{[1-Isobutanoyloxyethoxy]carbonylamino}propyl Sulfinic Acid

Solvents

diethyl ether

water

acetonitrile

Conditions

Workup

1. 1
   Washwashed with 0.1 M aqueous potassium bisulfate (3×100 mL)
2. 2
   OtherThe organic phase is separated
3. 3
   Dryingdried over anhydrous magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated in vacuo

Procedure

To a solution of 3-aminopropylsulfinic acid (10 mmol) and sodium bicarbonate (20 mmol) in water (40 mL) is added a solution of compound (17) (10 mmol) in acetonitrile (20 mL) over 1 min. The reaction is stirred at ambient temperature for 16 h. The reaction mixture is diluted with diethyl ether (100 mL) and washed with 0.1 M aqueous potassium bisulfate (3×100 mL). The organic phase is separated, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to afford the title compound (31) as a white solid.

Source