Ethyl chloroformate → N-(Ethoxycarbonyl)-D-norvaline

HRID 1694548Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1694548
[NH2:1][C@@H:2]([C:6]([OH:8])=[O:7])[CH2:3][CH2:4][CH3:5].Cl[C:10]([O:12][CH2:13][CH3:14])=[O:11]>[OH-].[Na+]>[CH2:13]([O:12][C:10]([NH:1][C@@H:2]([C:6]([OH:8])=[O:7])[CH2:3][CH2:4][CH3:5])=[O:11])[CH3:14]

Komponenten

4

Edukt 2

HCID 10928Ethyl chloroformateHCID 439575D-Norvaline

Produkt 1

HCID 59868837N-(Ethoxycarbonyl)-D-norvaline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14798Sodium HydroxideLösungsmittel2×

Versuchsvorschrift

D-Norvaline (10.0 g, 85.3 mmol) was dissolved in aqueous sodium hydroxide (4M, 25 mL). Ethyl chloroformate (10.6 mL, 111 mmol) and aqueous sodium hydroxide (4M, 25 mL) was added over 15 min. at 0° C. The reaction mixture was warmed to room temperature and stirred at this temperature for 4 h. The reaction mixture was washed with diethyl ether three times and then acidified with aqueous hydrochloric acid (2M). The product was extracted with diethyl ether three times. The combined organic phases were dried over magnesium sulphate and concentrated in vacuo to yield the title compound in quantitative yield.

Aufarbeitung

  1. washThe reaction mixture was washed with diethyl ether three times
  2. extractionThe product was extracted with diethyl ether three times
  3. dry with materialThe combined organic phases were dried over magnesium sulphate
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ab13a9fc1221452db35569b17ff61465
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158785B2

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