Acetylphenylalanine methyl ester → N-acetylphenylalanine aldehyde

HRID 1371260

Reaktionsgleichung

Reaktionsgleichung von HRID 1371260
C[O:2][C:3](=O)[C@H:4]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[NH:5][C:6](=[O:8])[CH3:7].[H-].C([Al+]CC(C)C)C(C)C>COCCOC.C1(C)C=CC=CC=1>[C:6]([NH:5][C@H:4]([CH:3]=[O:2])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:8])[CH3:7]

Komponenten

5

Edukt 2

HCID 704002Acetylphenylalanine methyl esterHCID 21225700Diisobutylaluminumhydride

Produkt 1

HCID 193217N-acetylphenylalanine aldehydeAusbeute 74,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

N-Acetylphenylalanine methyl ester (4.2 g, 19 mmol) is dissolved in ethylene glycol dimethyl ether. The solution is cooled to −70° C. and diisobutylaluminum hydride (25.3 mL of a 1.5M solution in toluene, 39 mmol) is added. The resulting reaction mixture is stirred at −70° C. for 2 hours. The reaction is quenched by addition of 2N hydrochloric acid. The mixture is extracted 4 times with cold ethyl acetate and 4 times with toluene. The extracts are combined, washed with brine and dried over magnesium sulfate. Concentration in vacuo followed by silica gel chromatography furnishes 2.7 g of a white solid. The NMR is as reported in the literature, Biochemistry, 18: 921–926 (1979).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. customThe reaction is quenched by addition of 2N hydrochloric acid
  3. extractionThe mixture is extracted 4 times with cold ethyl acetate and 4 times with toluene
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationConcentration in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-94035ab7620241518e18013fb8ecf6b4
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157426B2

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