Water → HCID 67076820, Verbindung

HRID 1348617

Reaktionsgleichung

Reaktionsgleichung von HRID 1348617
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][N:6]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2].C([N-]C(C)C)(C)C.[Li+].[C:30]1([CH2:36][CH:37]=[O:38])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.O>O1CCCC1>[CH2:1]([O:3][C:4](=[O:21])[CH:5]([N:6]([CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:37]([OH:38])[CH2:36][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH3:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 998PhenylacetaldehydeHCID 2724682Lithium diisopropylamideHCID 3553452Ethyl 2-(dibenzylamino)acetate

Produkt 1

HCID 67076820HCID 67076820, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 20 g (70.6 mmol) dibenzylamino-acetic acid ethyl ester in 240 ml tetrahydrofuran was stirred at −78° C. with 38.8 ml (77.6 mmol) lithium diisopropylamide (2M in heptane) for 30 minutes. 17.4 ml (77.6 mmol) phenylacetaldehyde were added and stirring was continued overnight. The mixture was allowed to warm to room temperature, water was added and most of the organic solvent was removed by distillation. About 20 g citric acid were dissolved in the aqueous residue. Extraction with ethylacetate and chromatography on silicagel with ethylacetate/heptane 1/5 yielded as first eluting fraction 5.4 g (19%) racemic (2S,3R and 2R,3S)-2-dibenzylamino-3-hydroxy-4-phenyl-butyric acid ethyl ester, MS m/e (%): 404.3 (M+H+, 100) and as second eluting fraction 4.1 g (15%) racemic (2R,3R and 2S,3S)-2-dibenzylamino-3-hydroxy-4-phenyl-butyric acid ethyl ester, MS m/e (%): 404.3 (M+H+, 100).

Aufarbeitung

  1. customwas removed by distillation
  2. dissolutionAbout 20 g citric acid were dissolved in the aqueous residue
  3. extractionExtraction with ethylacetate and chromatography on silicagel with ethylacetate/heptane 1/5

Quellen und Nachweise

ORD-Eintrag
ord-707a7759b4aa447388e0a5b5565c76f9
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07211573B2

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