Reaktion #7393

Reaktionsgleichung

N,N-diisopropylamine

Mixture 1

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

ethanol

→

title compound

tert-Butyl 2-(3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)butanoate

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe reaction mixture was filtered through Celite™
2. 2
   Einengenthe filtrate was concentrated under reduced pressure
3. 3
   Sonstigeto give a yellow gum
4. 4
   workup.STIRRINGstirred at room temperature for 24 h
5. 5
   WaschenThe mixture was washed with water
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   Sonstigeto yield an oil which
8. 8
   Sonstigewas partially purified
9. 9
   WaschenSPE (silica, eluting with cyclohexane:ethyl acetate 1:1)

Vorschrift

A mixture of Intermediate 112 [Mixture 1] (0.051 g), 10% palladium on carbon (0.01 g) and ethanol (5 ml) was stirred under an atmosphere of hydrogen for 18 h. The reaction mixture was filtered through Celite™ and the filtrate was concentrated under reduced pressure to give a yellow gum. The gum (0.034 g) in DCM (2 ml) was treated with 6-chloronaphthylsulphonyl chloride1 (0.04 g) and N,N-diisopropylamine (0.073 ml) and stirred at room temperature for 24 h. The mixture was washed with water and concentrated under reduced pressure to yield an oil which was partially purified using SPE (silica, eluting with cyclohexane:ethyl acetate 1:1) to give the title compound (0.043 g) as a white solid.

Quelle