Ethyl bromoacetate → N-((1R)-1-Phenylethyl)glycine ethyl ester

HRID 747917

Reaktionsgleichung

Reaktionsgleichung von HRID 747917
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:8]([O-])(=O)[C@@H:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)O.C([N:21](C(C)C)C(C)C)C>C1(C)C=CC=CC=1>[C:11]1([C@H:9]([NH:21][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH3:8])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

5

Edukt 3

HCID 7748Ethyl bromoacetateHCID 81531DiisopropylethylamineHCID 5460269(R)-Mandelate

Produkt 1

HCID 6455333N-((1R)-1-Phenylethyl)glycine ethyl esterAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Ethyl bromoacetate (4.14 g; 24.8 mmol) was treated with (R) α-methylbenzylamine (3 g, 24.8 mmol) and ethyldiisopropylamine (3.2 g; 24.8 mmol) in toluene (100 mL). After heating at reflux for 18 hours, the mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, 20% ethyl acetate/pentane) to provide the title compound (3.2 g, 63% yield). MS (DCl/NH3) m/z 208 (M+H)+.

Aufarbeitung

  1. temperatureAfter heating
  2. temperatureat reflux for 18 hours
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash chromatography (SiO2, 20% ethyl acetate/pentane)

Quellen und Nachweise

ORD-Eintrag
ord-11259bb170614753b0fccd882c74244b
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07399765B2

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