Reaction #7388

Reaction equation

tert-butyl (2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoate

potassium carbonate

benzyl-2-bromoacetate

→

title compound

Yield 115.5%

tert-butyl (2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl](2-benzyloxy-2-oxoethyl)amino}-2-oxopyrrolidin-1-yl)propanoate

Yield 115.5%

Solvents

DMF

Conditions

Workup

1. 1
   FiltrationThe reaction mixture was filtered
2. 2
   Concentrationconcentrated under reduced pressure
3. 3
   Otherthe residue partitioned between water and DCM
4. 4
   OtherThe organic layer was isolated
5. 5
   Dryingdried (over magnesium sulphate
6. 6
   Otherpurified by SPE (silica, cyclohexane:ethyl acetate 2:1)

Procedure

To a solution of tert-butyl (2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoate (1 g) in DMF (20 ml) was added potassium carbonate (0.92 g) and benzyl-2-bromoacetate (0.33 g), and the mixture was stirred under nitrogen at room temperature for 72 h. The reaction mixture was filtered, concentrated under reduced pressure, and the residue partitioned between water and DCM. The organic layer was isolated, dried (over magnesium sulphate and purified by SPE (silica, cyclohexane:ethyl acetate 2:1) to give the title compound (1.0 g) as a white solid.

Source