Reaktion #1807692

Reaktionsgleichung

2-(2-[4-(benzyloxy)phenoxy]-1-hydroxyethyl}-1-[N-(3-phenylpropionyl)-L-prolyl]pyrrolidine

pyridine

trifluoroacetic acid

DCC

→

title compound

Ausbeute 96.5%

(2S)-2-(4-Hydroxyphenoxyacetyl)-l-[N-(3-phenylpropionyl)-L-prolyl]pyrrolidine

Ausbeute 96.5%

Lösungsmittel

DMSO

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate
2. 2
   WaschenThe extract was washed with 1N hydrochloric acid, saturated aqueous solution of sodium bicarbonate and saturated brine
3. 3
   Trocknendried over anhydrous magnesium sulfate
4. 4
   Einengenconcentrated
5. 5
   SonstigeThe residue was purified by silica gel column chromatography (eluate: chloroform-methanol)

Vorschrift

To a solution of (2S)-2-{2-(2-[4-(benzyloxy)phenoxy]-1-hydroxyethyl}-1-[N-(3-phenylpropionyl)-L-prolyl]pyrrolidine (1.81 g) in DMSO (30 ml) were added pyridine (0.3 ml), trifluoroacetic acid (0.15 ml) and DCC (1.2 g), and the mixture was stirred at room temperature for 4 hours. The reaction mixture was poured into ice-water and extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid, saturated aqueous solution of sodium bicarbonate and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (eluate: chloroform-methanol) to give 1.45 g of the title compound.

Quelle