L-Valine → (2S)-3-methyl-2-(2-phenylacetamido)butanoic acid

HRID 860368

Reaktionsgleichung

Reaktionsgleichung von HRID 860368
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4].[OH-].[Na+].[C:11]1([CH2:17][C:18](Cl)=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[C:11]1([CH2:17][C:18]([NH:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4])=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

4

Edukt 3

HCID 6287L-ValineHCID 7679Phenylacetyl chlorideHCID 14798Sodium Hydroxide

Produkt 1

HCID 853958(2S)-3-methyl-2-(2-phenylacetamido)butanoic acidAusbeute 75 %

Versuchsvorschrift

To a stirred solution of 5.15 g (44 mmol) of valine (Bachem) in 50 mL (100 mmol) of 2N NaOH cooled to 0° C. was added dropwise 5.3 mL (40 mmol) of phenylacetyl chloride (Aldrich). A colorless oil precipitated. The reaction mixture was allowed to warm to room temperature and stirred for 18 hours, washed with 50 mL diethyl ether, acidified to pH 2–3 with aqueous HCl. The white precipitate formed was filtered off, washed thoroughly with water, followed by diethyl ether to give 7.1 g (30 mmol, 69% yield) of the title compound.

Aufarbeitung

  1. customA colorless oil precipitated
  2. washwashed with 50 mL diethyl ether
  3. customThe white precipitate formed
  4. filtrationwas filtered off
  5. washwashed thoroughly with water

Quellen und Nachweise

ORD-Eintrag
ord-737ff0ee57b0407dafaed4ccb01478f6
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07153847B2

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