Reaktion #7408

Reaktionsgleichung

Piperidine

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

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

HOBT

→

title compound

Ausbeute 8.6%

6-Chloro-N-methyl-N-{(3S)-1-[(1S)-1-methyl-2-oxo-2-piperidin-1-ylethyl]-2-oxopyrrolidin-3-yl}naphthalene-2-sulfonamide

Ausbeute 8.6%

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
   SonstigeThe residue was purified

Vorschrift

To a solution of (2S)-2{(3S)-3-[[(6-chloro-2-naphthyl)sulfonyl](methyl)amino]-2-oxopyrrolidin-1-yl}propanoic acid (0.020 g) in DCM (2 ml) were added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.011 g), HOBT (0.007 g) and triethylamine (0.020 ml) and the mixture was stirred at room temperature for 30 min. Piperidine (0.006 ml) 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 purified using mass directed preparative h.p.l.c. to give the title compound (0.002 g) as a colourless gum.

Quelle