Reaction #1994242

Reaction equation

L-glutamic acid

acetic anhydride

KOH

triethylamine

→

N,5-diacetylpyrrolidin-2-one

Conditions

Workup

1. 1
   OtherThe crude reaction product
2. 2
   Concentrationis concentrated under reduced pressure (rotary evaporator and vane pump)
3. 3
   Washthe organic layer is then washed five times with 100 mL of deionized water
4. 4
   workup.ADDITIONtreated over animal carbon
5. 5
   OtherThe product obtained
6. 6
   Otherafter evaporation of the solvent
7. 7
   Otheris purified by crystallization from petroleum ether/CH2Cl2
8. 8
   WashThe crystals are rinsed with petroleum ether

Procedure

A 500-mL round bottom flask under argon atmosphere is charged with L-glutamic acid 4 (21 g, 0.143 mol), a catalytic amount of N,N-dimethylaminopyridine (150 mg, 1×10−3 mol), acetic anhydride (75 mL) and triethylamine previously distilled over KOH (75 mL). The reaction mixture is maintained at 60° C. for 16 hours. The progression of the reaction is followed by TLC (eluent: ethyl acetate/petroleum ether at a ratio of 8/2). The crude reaction product is concentrated under reduced pressure (rotary evaporator and vane pump) and then taken up in 200 mL of dichloromethane; the organic layer is then washed five times with 100 mL of deionized water and then treated over animal carbon. The product obtained after evaporation of the solvent is purified by crystallization from petroleum ether/CH2Cl2. The crystals are rinsed with petroleum ether.

Source