Réaction #7402

Équation de réaction

Morpholine

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

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

HOBT

→

title compound

6-Chloro-N-{(3S)-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-yl}-N-(2-oxobutyl)naphthalene-2-sulfonamide

Solvants

DCM

triethylamine

Conditions de réaction

Traitement

1. 1
   AutreThe mixture was partitioned between DCM and water
2. 2
   ExtractionThe aqueous layer was re-extracted with DCM
3. 3
   Séchagedried (over magnesium sulphate) organic extracts
4. 4
   Concentrationwere concentrated under reduced pressure
5. 5
   AutreThe residue was purified

Mode opératoire

To a solution of (2S)-2-{(3S)-3-[[(6-chloro-2-naphthyl)sulfonyl](2-oxobutyl)amino]-2-oxopyrrolidin-1-yl}propanoic acid (0.035 g) in DCM (2 ml) were added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.044 g), HOBT (0.031 g) and triethylamine (0.064 ml) and the mixture was stirred at room temperature for 30 min. Morpholine (0.02 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 (0.008 g) as a white solid.

Source