Zurück
HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 58867Erstellt: 26. Oktober 2026

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

https://huagongshe.com/reaction/58867

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktTrifluoroacetic acidHCID 6422—
EduktSodium BicarbonateHCID 516892—
EduktBenzyl (2S,3R)-2-(Boc-amino)-3-hydroxy-3-(4-methoxyphenyl)propanoateHCID 131737022—
LösungsmittelDichloromethaneHCID 6344—
Produkt(2S,3R)-benzyl 2-amino-3-hydroxy-3-(4-methoxyphenyl)propanoateHCID 117607803101,8%

Reaktionsbedingungen

Temperatur0 °C

Reaktionsschritte

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.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS09434761B2
Quelldatensatzuspto-grants-2016_09
ORD IDord-c75d3cc5061c4a09b85a397049c27247
Quellennotizuspto-grants-2016_09