Triethylamine → 2-(Cyclopropanecarbonyl-amino)-propionic acid ethyl ester

HRID 1158982

Reaktionsgleichung

Reaktionsgleichung von HRID 1158982
Cl.[CH2:2]([O:4][C:5](=[O:9])[C@H:6]([CH3:8])[NH2:7])[CH3:3].C(N(CC)CC)C.[CH:17]1([C:20](Cl)=[O:21])[CH2:19][CH2:18]1.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:2]([O:4][C:5](=[O:9])[CH:6]([NH:7][C:20]([CH:17]1[CH2:19][CH2:18]1)=[O:21])[CH3:8])[CH3:3]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 516892Sodium BicarbonateHCID 2724356L-Alanine, ethyl ester, hydrochloride (1:1)

Produkt 1

HCID 586367092-(Cyclopropanecarbonyl-amino)-propionic acid ethyl esterAusbeute 96,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of L-alanine ethyl ester hydrochloride (50 g, 325 mmol) in anhydrous dichloromethane (800 mL) added triethylamine (65.8 g, 650 mmol) and stirred at room temperature for 30 minutes. To the reaction mixture cyclopropanecarbonyl chloride (50.96 g, 0.487 mole) was slowly added and stirred at room temperature for overnight. The reaction mixture was then poured into a cold solution of saturated aqueous sodium bicarbonate, and the crude product extracted with dichloromethane, dried over anhydrous magnesium sulfate. Evaporation of the solvent gave a crude residue, which was purified by column chromatography on silica gel using a mixture of ethyl acetate:hexane (1:1) as eluant to give 2-(cyclopropanecarbonyl-amino)-propionic acid ethyl ester (163) (58.0 g, 96% yield).

Aufarbeitung

  1. stirringstirred at room temperature for overnight
  2. extractionthe crude product extracted with dichloromethane
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customEvaporation of the solvent
  5. customgave a crude residue, which
  6. customwas purified by column chromatography on silica gel using
  7. additiona mixture of ethyl acetate:hexane (1:1) as eluant

Quellen und Nachweise

ORD-Eintrag
ord-69d17007803b427585abb2ed6ba25eae
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07812037B2

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