Lithium hydroxide, monohydrate → 1-Cbz-3-azetidineacetic acid

HRID 1596184Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1596184
[CH2:1]([O:8][C:9]([N:11]1[CH2:14][CH:13]([CH2:15][C:16]([O:18]CC)=[O:17])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+]>O>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH:13]([CH2:15][C:16]([OH:18])=[O:17])[CH2:14]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 69944833HCID 69944833, Verbindung

Produkt 1

HCID 404294021-Cbz-3-azetidineacetic acidAusbeute 98,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 3-ethoxycarbonylmethylazetidine-1-carboxylic acid benzyl ester (0.30 g, 1.1 mmol), and lithium hydroxide monohydrate (0.091 g, 2.2 mmol) in TBF (3 mL) and water (1 mL) was stirred under argon at room temperature for 1 hr. After acidification with 2 M aqueous hydrochloric acid (10 mL), the reaction mixture was extracted with ethyl acetate (3×20 ml). The combined ethyl acetate layers were washed with water (10 mL), brine (10 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to give 0.27 g of the title compound.

Aufarbeitung

  1. extractionAfter acidification with 2 M aqueous hydrochloric acid (10 mL), the reaction mixture was extracted with ethyl acetate (3×20 ml)
  2. washThe combined ethyl acetate layers were washed with water (10 mL), brine (10 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-73ff499ea5da4b9bb8089b6cee798909
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06291457B1

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