Reaktion #7406

Reaktionsgleichung

Ethyl pipecolinate

(2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoic acid

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

HOBT

→

title compound

Ausbeute 21.9%

1-[(2S)-2-((3S)-3-{[(6-Chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoyl]piperidine-2-carboxylic acid

Ausbeute 21.9%

Lösungsmittel

DCM

triethylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was partitioned between DCM and water
2. 2
   ExtraktionThe aqueous layer was re-extracted with DCM
3. 3
   Trocknendried (over magnesium sulphate) organic extracts
4. 4
   Einengenwere concentrated under reduced pressure
5. 5
   workup.DISSOLUTIONThe residue was then dissolved in a mixture of THF (1 ml) and water (1 ml)
6. 6
   workup.ADDITIONtreated with lithium hydroxide (0.005 g)
7. 7
   workup.STIRRINGstirred at room temperature for 18 h
8. 8
   Einengenconcentrated under reduced pressure
9. 9
   SonstigeThe residue was purified
10. 10
    WaschenSPE (aminopropyl stationary phase, washed with methanol and eluted with 10% hydrochloric acid in methanol)

Vorschrift

To a solution of (2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoic acid (0.025 g) in DCM (10 ml) were added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.036 g), HOBT (0.026 g) and triethylamine (0.026 ml) and the mixture was stirred at room temperature for 30 min. Ethyl pipecolinate (0.030 g) was added and the resultant mixture stirred at room temperature for 16 h. The mixture was partitioned between DCM and water. The aqueous layer was re-extracted with DCM and the combined, dried (over magnesium sulphate) organic extracts were concentrated under reduced pressure. The residue was then dissolved in a mixture of THF (1 ml) and water (1 ml), treated with lithium hydroxide (0.005 g) and stirred at room temperature for 18 h. The reaction mixture was acidified to pH5 using hydrochloric acid (2N) and concentrated under reduced pressure. The residue was purified using SPE (aminopropyl stationary phase, washed with methanol and eluted with 10% hydrochloric acid in methanol) to give the title compound (0.007 g) as white solid.

Quelle