Reaktion #5507

Reaktionsgleichung

hydrochloric acid

Diethyl 2-oxo-1-azacyclotetradecane-3,14-dicarboxylate

Sodium hydroxide

→

2-oxo-1-azacyclotetradecane-3,14-dicarboxylic acid

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONmixture of both diastereomers)
2. 2
   Sonstigepartitioned between ethyl acetate and water
3. 3
   ExtraktionThe aqueous phase is extracted several times with ethyl acetate
4. 4
   Trocknenthe combined organic layers are dried (Na2SO4)
5. 5
   Sonstigethe solvent is evaporated

Vorschrift

Diethyl 2-oxo-1-azacyclotetradecane-3,14-dicarboxylate (1.14 g, 3.2 mmol; mixture of both diastereomers) is dissolved in ethanol (32.0 mL). Sodium hydroxide (9.6 mL of a 1N aqueous solution, 9.6 mmol) is added dropwise, and the solution is stirred at room temperature for 3 hours. The reaction is then acidified to pH 3 with 1N hydrochloric acid, and partitioned between ethyl acetate and water. The aqueous phase is extracted several times with ethyl acetate, the combined organic layers are dried (Na2SO4), and the solvent is evaporated to give both diastereomers of 2-oxo-1-azacyclotetradecane-3,14-dicarboxylic acid.

Quelle