Ethyl 2-(benzylamino)propanoate → Methyl 4-(benzyl(1-ethoxy-1-oxopropan-2-yl)amino)butanoate

HRID 453147Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 453147
[CH2:1]([O:3][C:4](=[O:15])[CH:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:6])[CH3:2].O=[C:17]([CH2:22][CH3:23])[C:18]([O:20][CH3:21])=[O:19]>ClCCCl>[CH3:21][O:20][C:18](=[O:19])[CH2:17][CH2:22][CH2:23][N:7]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH:5]([C:4]([O:3][CH2:1][CH3:2])=[O:15])[CH3:6]

Komponenten

4

Edukt 2

HCID 222273Ethyl 2-(benzylamino)propanoateHCID 5451272-Ketobutyric acid methyl ester

Produkt 1

HCID 67423852Methyl 4-(benzyl(1-ethoxy-1-oxopropan-2-yl)amino)butanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

2-Benzylamino-propionic acid ethyl ester (1.4 g, 6.7 mmol), methyl oxo-butanoate (1.7 g, 13.5 mmol), LEA (1.9 mL, 13.5 mmol) and NaBH(Oac)3 (2.9 g, 13.5 mmol) are taken up in 1,2-DCE (35 mL) and stirred at rt for 4 h. The reaction is partitioned between DCM and saturated aqueous NaHCO3. The organic layer is removed, dried over anhydrous Na2SO4, and concentrated in vacuo. The crude residue is used without further purification. MS (ESI) m/z 308.3 (M+1).

Aufarbeitung

  1. customThe reaction is partitioned between DCM and saturated aqueous NaHCO3
  2. customThe organic layer is removed
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude residue is used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-e4cfdc9950314a399af48d89d63d6364
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492393B2

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