Reaktion #87188

Reaktionsgleichung

(S)-2-((tert-butoxycarbonyl)amino)-3-(pyridin-2-yl)propanoic acid

BnCOCl

→

(S)-benzyl 2-((tert-butoxycarbonyl)amino)-3-(pyridin-2-yl)propanoate

Ausbeute 42.0%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to ambient temperature overnight at which time it
2. 2
   Sonstigewas quenched with sodium bicarbonate (sat.)
3. 3
   Extraktionextracted with ethyl acetate (2×)
4. 4
   Trocknendried with sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   SonstigePurification by column chromatography (0-50% ethyl acetate/hexanes+1% TEA)

Vorschrift

To (S)-2-((tert-butoxycarbonyl)amino)-3-(pyridin-2-yl)propanoic acid (1.00 g, 3.76 mmol) in DCM (10 mL) was added TEA (0.974 mL, 7.52 mmol) and DMAP (23 mg, 0.188 mmol) and the reaction mixture was cooled to 0° C. and BnCOCl (635 mL, 4.51 mmol) was added via an addition funnel over 20 min. The mixture was allowed to warm to ambient temperature overnight at which time it was quenched with sodium bicarbonate (sat.), extracted with ethyl acetate (2×), dried with sodium sulfate, filtered, and concentrated. Purification by column chromatography (0-50% ethyl acetate/hexanes+1% TEA) provided (S)-benzyl 2-((tert-butoxycarbonyl)amino)-3-(pyridin-2-yl)propanoate (0.558 g, 42%) as a light brown solid. MS (EI) for C20H24N2O4, found 257.2 [M-Boc]+.

Quelle