Reaction #657272

Reaction equation

N-hydroxysuccinimide

dicyclohexylcarbodiimide

(Pyrimidin-2-ylsulfanyl)-acetic acid

→

(Pyrimidin-2-ylsulfanyl)-acetic acid-(2,5-dioxo-pyrrolidine-1-yl)-ester

Solvents

DMF

Conditions

Workup

1. 1
   FiltrationThe residue was filtered
2. 2
   Otherthe filtrate was evaporated in vacuo to dryness
3. 3
   workup.DISSOLUTIONThe remaining product was dissolved
4. 4
   Temperatureunder reflux in 400 ml ethyl acetate
5. 5
   Filtrationthe hot solution was filtered
6. 6
   Otherthe mixture was subjected to a chromatographic purification (Florisil)
7. 7
   OtherThe compound was then recrystallised from ethyl acetate

Procedure

12.31 g (107 mMol) N-hydroxysuccinimide and 22.70 g (110 mMol) dicyclohexylcarbodiimide were added at −35° C. to a solution of 18.27 g (107 mMol) (Pyrimidin-2-ylsulfanyl)-acetic acid (a) dissolved in 200 ml DMF. The reaction mixture was stirred for 16 h under argon. The residue was filtered and the filtrate was evaporated in vacuo to dryness. The remaining product was dissolved under reflux in 400 ml ethyl acetate, the hot solution was filtered and the mixture was subjected to a chromatographic purification (Florisil) using ethyl acetate. The compound was then recrystallised from ethyl acetate.

Source