Reaktion #7395

Reaktionsgleichung

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

HOBT

trifluoroacetic acid

piperidine

tert-Butyl (2S)-2-[(3S)-3-({[(E)-2-(4-chlorophenyl)ethenyl]sulfonyl}amino)-2-oxopyrrolidin-1-yl]propanoate

→

title compound

Ausbeute 21.3%

(E)-2-(4-Chlorophenyl)-N-{(3S)-1-[(1S)-1-methyl-2-oxo-2-piperidin-1-ylethyl]-2-oxopyrrolidin-3-yl}ethenesulfonamide

Ausbeute 21.3%

Lösungsmittel

triethylamine

DCM

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe mixture was then concentrated under reduced pressure
2. 2
   Sonstigeto give an oil which
3. 3
   workup.STIRRINGAfter the solution had been stirred at room temperature for 30 min
4. 4
   EinengenThe mixture was concentrated under reduced pressure
5. 5
   Sonstigethe residue partitioned between DCM and water
6. 6
   WaschenThe organic component was washed with water and brine
7. 7
   Einengenconcentrated under reduced pressure
8. 8
   SonstigeThe residue was purified
9. 9
   WaschenSPE (silica, eluting with cyclohexane; cyclohexane:ethyl acetate 4:1, 1:1, 1:4; ethyl acetate; methanol:ethyl acetate 1:10; methanol)

Vorschrift

tert-Butyl (2S)-2-[(3S)-3-({[(E)-2-(4-chlorophenyl)ethenyl]sulfonyl}amino)-2-oxopyrrolidin-1-yl]propanoate (0.192 g) was dissolved in DCM (2 ml) and treated with trifluoroacetic acid (2 ml) and stirred at room temperature for 2 h. The mixture was then concentrated under reduced pressure to give an oil which was subsequently dissolved in DCM (5 ml) and treated with 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.256 g), HOBT (0.184 g) and triethylamine (0.375 ml). After the solution had been stirred at room temperature for 30 min, piperidine (0.133 ml) was added and the resultant mixture stirred for a further 20 h. The mixture was concentrated under reduced pressure and the residue partitioned between DCM and water. The organic component was washed with water and brine, and concentrated under reduced pressure. The residue was purified using SPE (silica, eluting with cyclohexane; cyclohexane:ethyl acetate 4:1, 1:1, 1:4; ethyl acetate; methanol:ethyl acetate 1:10; methanol) to give the title compound (0.042 g) as a white solid.

Quelle