Реакция #87188

Уравнение реакции

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

BnCOCl

→

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

Выход 42.0%

Растворители

DCM

Условия реакции

Обработка

1. 1
   Температураto warm to ambient temperature overnight at which time it
2. 2
   Другоеwas quenched with sodium bicarbonate (sat.)
3. 3
   Экстракцияextracted with ethyl acetate (2×)
4. 4
   Сушкаdried with sodium sulfate
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеconcentrated
7. 7
   ДругоеPurification by column chromatography (0-50% ethyl acetate/hexanes+1% TEA)

Методика

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]+.

Источник