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Hydrochloric Acid → HCID 14503313, Verbindung

HRID 396866
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 396866
C(OC([NH:11][C@@H:12]([CH:20]([CH3:22])[CH3:21])C(OC(=O)C)C#N)=O)C1C=CC=CC=1.Cl.C1([O:30]C)C=CC=CC=1.[O:32]1[CH2:37][CH2:36][O:35]CC1>>[NH2:11][C@@H:12]([CH:20]([CH3:22])[CH3:21])[CH:36]([OH:35])[C:37]([OH:32])=[O:30]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 4

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 312751,4-DioxaneHCID 228716173-(S)-[(benzyloxycarbonyl)amino]-2-acetoxy-4-methylpentanenitrile

Produkt 1

HCID 14503313HCID 14503313, VerbindungAusbeute 75 %

Versuchsvorschrift

To a solution containing 3-(S)-[(benzyloxycarbonyl)amino]-2-acetoxy-4-methylpentanenitrile (see example 1 of WO 96/16080) (15.2 g, 50.0 mmol) in 183 ml of dioxane was added 183 mL of concentrated hydrochloric acid and 7.45 mL of anisole. The reaction mixture was heated to reflux overnight. The hydrolysis reaction was allowed to cool to room temperature and then concentrated in vacuo. The resulting aqueous solution was extracted with ether (2×). The aqueous phase was placed on a Dowex 50X8-100 column (H+ form, preeluted with deionized water to pH=7). The column was eluted with 2.0 N ammonium hydroxide and the pure fractions concentrated to afford 5.53 g (75%) of 3-(S)-amino-2-(R,S)-hydroxy-4-methylpentanoic acid as a pale yellow solid. FAB MS [M+H] m/z; Calcd: 148, Found: 148.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight
  3. customThe hydrolysis reaction
  4. concentrationconcentrated in vacuo
  5. extractionThe resulting aqueous solution was extracted with ether (2×)
  6. washThe column was eluted with 2.0 N ammonium hydroxide
  7. concentrationthe pure fractions concentrated

Quellen und Nachweise

ORD-Eintrag
ord-579f9e0937e240eb983454117fb76a51
Quelldatensatz
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06608175B2

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