Reaktion #50655

Reaktionsgleichung

carbobenzyloxy-D,L-alanine

N-aminopyrrole

DCC

→

product

Ausbeute 66.0%

(±)-Phenylmethyl-[1-methyl-2-oxo-2-(1H-pyrrol-1-ylamino)ethyl]carbamate

Ausbeute 66.0%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationthe reaction mixture was filtered through a pad of celite
2. 2
   Waschenthe solid DCU was washed with DCM
3. 3
   SonstigeConcentration of the filtrate gave the crude product
4. 4
   SonstigePurification via flash column chromatography (silica gel, 30% ethyl acetate/hexane)

Vorschrift

To a stirred solution consisting of carbobenzyloxy-D,L-alanine (10.0 g) and N-aminopyrrole (3.68 g) in dry DCM (224 ml) was added DCC (9.71 g) at room temperature under nitrogen. After stirring for 20 hours, the reaction mixture was filtered through a pad of celite and the solid DCU was washed with DCM. Concentration of the filtrate gave the crude product. Purification via flash column chromatography (silica gel, 30% ethyl acetate/hexane) afforded 8.50 g of the product as a solid, m.p. 153°-155° C.

Quelle