تفاعل #87188

معادلة التفاعل

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

BnCOCl

→

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

المردود 42.0%

المذيبات

DCM

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto warm to ambient temperature overnight at which time it
2. 2
   أخرىwas quenched with sodium bicarbonate (sat.)
3. 3
   استخلاصextracted with ethyl acetate (2×)
4. 4
   تجفيفdried with sodium sulfate
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated
7. 7
   أخرىPurification by column chromatography (0-50% ethyl acetate/hexanes+1% TEA)

الإجراء التجريبي

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]+.

المصدر