Methanol → 4-Amino-2(S)-hydroxybutyric acid ethyl ester, hydrochloride

HRID 1587982

Reaktionsgleichung

Reaktionsgleichung von HRID 1587982
C(OC([NH:11][CH2:12][CH2:13][C@H:14]([OH:18])[C:15]([OH:17])=[O:16])=O)C1C=CC=CC=1.S(Cl)([Cl:21])=O.[C:23](OCC)(=O)[CH3:24].CO>C(O)C.[Pd]>[ClH:21].[CH2:23]([O:17][C:15](=[O:16])[C@@H:14]([OH:18])[CH2:13][CH2:12][NH2:11])[CH3:24]

Komponenten

7

Edukt 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 24386Thionyl ChlorideHCID 2733930(S)-2-Hydroxy-4-(((phenylmethoxy)carbonyl)amino)butyric acid

Produkt 1

HCID 1317179804-Amino-2(S)-hydroxybutyric acid ethyl ester, hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel2×

Versuchsvorschrift

Add 4-benzyloxycarbonylamino-2(S)-hydroxybutyric acid (2.57 g) to absolute ethanol (30 ml) containing thionyl chloride (2.0 ml) and heat the resulting mixture under reflux for 20 hours. Cool, filter and concentrate the reaction mixture in vacuo to give a pale yellow oil. Chromatograph this oil on a column of silica gel (500 ml) using ethyl acetate as eluant to obtain a yellow oil, [α]D26 =+0.4° (MeOH). Hydrogenate the product (1.4 g) in absolute ethanol (50 ml) containing 10% Pd/C (0.50 g) at 50 psi for 2 hours. Filter the mixture and concentrate the mixture in vacuo to give the title compound as an oil.

Aufarbeitung

  1. temperatureheat the resulting mixture
  2. temperatureunder reflux for 20 hours
  3. temperatureCool
  4. filtrationfilter
  5. concentrationconcentrate the reaction mixture in vacuo
  6. customto give a pale yellow oil
  7. filtrationFilter the mixture
  8. concentrationconcentrate the mixture in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d63c0d21baef430cb46e78496d6a25ba
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05219886

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