Reaktion #158072

Reaktionsgleichung

(R)-ethyl 3-amino-4-(3′-chlorobiphenyl-4-yl)butanoate hydrochloride

ethyl 2-chloro-2-oxoacetate

→

(R)-ethyl 4-(3′-chlorobiphenyl-4-yl)-3-(2-ethoxy-2-oxoacetamido)butanoate

Ausbeute 83.8%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction is quenched with H2O
2. 2
   workup.ADDITIONthe crude is diluted with EtOAc
3. 3
   WaschenThe organic layer is washed with brine
4. 4
   Trocknendried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   SonstigeThe obtained residue is purified by flash column chromatography on silica gel (eluent: heptane/EtOAc=70:30 to 50:50)

Vorschrift

To a solution of (R)-ethyl 3-amino-4-(3′-chlorobiphenyl-4-yl)butanoate hydrochloride (500 mg, 1.57 mmol) in DMF (11 mL) is added TEA (0.23 mL, 1.65 mmol) and ethyl 2-chloro-2-oxoacetate (0.18 mL, 1.57 mmol) at room temperature. After stirring for 1 hour at room temperature, the reaction is quenched with H2O, and the crude is diluted with EtOAc. The organic layer is washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The obtained residue is purified by flash column chromatography on silica gel (eluent: heptane/EtOAc=70:30 to 50:50) to give (R)-ethyl 4-(3′-chlorobiphenyl-4-yl)-3-(2-ethoxy-2-oxoacetamido)butanoate (550 mg). HPLC retention time=1.88 minutes (condition A); MS (m+1)=418.3

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