반응 #87188

반응 방정식

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

BnCOCl

→

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

수율 42.0%

용매

DCM

반응 조건

후처리

1. 1
   온도to warm to ambient temperature overnight at which time it
2. 2
   기타was quenched with sodium bicarbonate (sat.)
3. 3
   추출extracted with ethyl acetate (2×)
4. 4
   건조dried with sodium sulfate
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   기타Purification by column chromatography (0-50% ethyl acetate/hexanes+1% TEA)

실험 절차

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]+.

출처