Dicyclohexylcarbodiimide → N-(4-methoxycarbonyl-2-methylbutanoyl)-L-alanine benzyl ester

HRID 262276Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 262276
[CH3:1][O:2][C:3]([CH2:5][CH2:6][CH:7]([CH3:11])[C:8]([OH:10])=O)=[O:4].[CH2:12]([O:19][C:20](=[O:24])[C@H:21]([CH3:23])[NH2:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.OC1C2N=NNC=2C=CC=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[CH2:12]([O:19][C:20](=[O:24])[C@H:21]([CH3:23])[NH:22][C:8](=[O:10])[CH:7]([CH3:11])[CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

6

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 726858benzyl (2S)-2-aminopropanoateHCID 131928974-Carbomethoxy-2-methylbutanoic acidHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 22804619N-(4-methoxycarbonyl-2-methylbutanoyl)-L-alanine benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-methoxycarbonyl-2-methylbutanoic acid (3.1 g.), L-alanine benzyl ester (3.58 g.) and hydroxybenzotriazole (2.7 g.) are dissolved in dichloromethane. The solution is chilled in the ice bath and dicyclohexylcarbodiimide (4.12 g.) is added. After stirring 15 minutes in the ice bath and 18 hours at room temperature the precipitate is filtered off and the filtrate is concentrated to dryness. The residue is dissolved in ethyl acetate and washed neutral. The organic phase is dried over magnesium sulfate and concentrated to dryness to yield N-(4-methoxycarbonyl-2-methylbutanoyl)-L-alanine benzyl ester.

Aufarbeitung

  1. additionis added
  2. filtrationis filtered off
  3. concentrationthe filtrate is concentrated to dryness
  4. dissolutionThe residue is dissolved in ethyl acetate
  5. washwashed neutral
  6. dry with materialThe organic phase is dried over magnesium sulfate
  7. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-58e48a7467074ebdaf5c471094cf7c7f
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04153725

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