Réaction #87145

Équation de réaction

NaHCO3

(2S,3R)-benzyl 2-((tert-butoxycarbonyl)amino)-3-hydroxy-3-(4-methoxyphenyl)propanoate

TFA

→

(2S,3R)-benzyl 2-amino-3-hydroxy-3-(4-methoxyphenyl)propanoate

Rendement 101.8%

Solvants

DCM

DCM

Conditions de réaction

Traitement

1. 1
   Autrethe two layers were separated
2. 2
   ExtractionThe aqueous layer were extracted with DCM (100 mL×2)
3. 3
   Séchagethe combined organics were dried over anhydrous sodium sulfate
4. 4
   Concentrationconcentrated

Mode opératoire

To (2S,3R)-benzyl 2-((tert-butoxycarbonyl)amino)-3-hydroxy-3-(4-methoxyphenyl)propanoate (3.0 g, 7.5 mmol) in DCM (30 mL) was added TFA (15 mL) and the mixture was stirred at 0° C. After 30 min it was diluted with DCM (100 mL). Saturated aqueous NaHCO3 (100 mL) was added and the two layers were separated. The aqueous layer were extracted with DCM (100 mL×2) and the combined organics were dried over anhydrous sodium sulfate and concentrated to afford crude (2S,3R)-benzyl 2-amino-3-hydroxy-3-(4-methoxyphenyl)propanoate (2.3 g, quant.) as an oil, which was used directly in the next step without further purification.

Source