Reaktion #7412

Reaktionsgleichung

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

trifluoroacetic acid

1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride

HOBT

N-piperidin-3-ylbenzamide

→

title compound

Ausbeute 55.2%

N-[1-((2R)-2-{(3S)-3-[[(6-Chloro-2-naphthyl)sulfonyl](methyl)amino]-2-oxopyrrolidin-1-yl}propanoyl)piperidin-3-yl]benzamide

Ausbeute 55.2%

Lösungsmittel

DCM

triethylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe mixture was then concentrated under reduced pressure
2. 2
   Sonstigeto give an oil which
3. 3
   workup.STIRRINGAfter stirring at room temperature for 1 h
4. 4
   workup.STIRRINGstirring
5. 5
   workup.WAITwas continued for 16 h
6. 6
   SonstigeThe reaction mixture was partitioned between DCM and water
7. 7
   ExtraktionThe organic extract
8. 8
   Einengenwas concentrated under reduced pressure
9. 9
   Sonstigethe residue purified
10. 10
    WaschenSPE (silica, eluting with cyclohexane:ethyl acetate 3:1, 1:1, 1:3, ethyl acetate)

Vorschrift

A solution of tert-butyl (2R)-2-{(3S)-3-[[(6-chloro-2-naphthyl)sulfonyl](methyl)amino]-2-oxopyrrolidin-1-yl}propanoate (0.017 g) in DCM (0.5 ml) was treated with trifluoroacetic acid (0.5 ml) and stirred at room temperature for 2 h. The mixture was then concentrated under reduced pressure to give an oil which was subsequently treated with 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.01 g), HOBT (0.007 g) and triethylamine (0.020 ml). After stirring at room temperature for 1 h, N-piperidin-3-ylbenzamide (0.010 g) was added and stirring was continued for 16 h. The reaction mixture was partitioned between DCM and water. The organic extract was concentrated under reduced pressure and the residue purified using SPE (silica, eluting with cyclohexane:ethyl acetate 3:1, 1:1, 1:3, ethyl acetate) to give the title compound (0.012 g) as a pale yellow gum.

Quelle