Reaction #66552

Reaction equation

TFA

ethyl JV-benzylglycinate

DCC

aminobutyric acid

→

title compound

(3S)-3-Ethyl-1-(phenylmethyl)-2,5-piperazinedione

Solvents

DCM

DCM

Conditions

Workup

1. 1
   Filtrationfiltered
2. 2
   Concentrationthe concentrated
3. 3
   Otherto give an oil
4. 4
   ConcentrationThe solution was concentrated under reduced pressure
5. 5
   workup.STIRRINGThe residue was stirred in saturated aq NaHCO3 (125 ml)
6. 6
   workup.WAITEtOAc (125 ml) for 6 h
7. 7
   OtherThe organics were separated
8. 8
   Dryingdried (Na2SO4)
9. 9
   Concentrationconcentrated

Procedure

To a solution of DCC (5.07 g) in DCM (140 mL) at 0° C. was added N—BOC-L-□-aminobutyric acid (5 g) followed by ethyl JV-benzylglycinate (4.6 mL) dropwise. The resulting solution was stirred at 0° C. for 2 h and RT 1 h, filtered and the concentrated to give an oil. This was dissolved in DCM (100 mL) and TFA (100 ml) and stirred for 1 h. The solution was concentrated under reduced pressure. The residue was stirred in saturated aq NaHCO3 (125 ml) and EtOAc (125 ml) for 6 h. The organics were separated, dried (Na2SO4), and concentrated to give the sub title compound as a white solid. (5.68 g).

Source