Reaktion #319312

Reaktionsgleichung

ethyl 3-[(4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-4-isobutyloxazolidin-5-yl]-2-[2-(2-tetrahydropyranyloxy)ethyl]-2-propenoate

water

hydrochloric acid

→

3-[(4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-4-isobutyloxazolidin-5yl]-2-[2-(2-tetrahydropyranyloxy)ethyl]-2-propenoic acid

Lösungsmittel

ethanol water

hexane ethyl acetate

potassium hydroxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was cooled to 0° C.
2. 2
   Extraktionextracted three times with 15 ml of ethyl acetate
3. 3
   WaschenThe ethyl acetate layer was washed sequentially with water
4. 4
   Trocknena saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate
5. 5
   workup.DISTILLATIONThen the solvent was distilled off under reduced pressure

Vorschrift

400 mg of ethyl 3-[(4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-4-isobutyloxazolidin-5-yl]-2-[2-(2-tetrahydropyranyloxy)ethyl]-2-propenoate was dissolved in 1.93 ml of an ethanol/water (10/1) solution of 2N potassium hydroxide, and the solution was stirred overnight at room temperature. 24 ml of water was added thereto, and the mixture was cooled to 0° C., then neutralized with 1N hydrochloric acid and extracted three times with 15 ml of ethyl acetate. The ethyl acetate layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. Then the solvent was distilled off under reduced pressure to obtain 3-[(4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-4-isobutyloxazolidin-5yl]-2-[2-(2-tetrahydropyranyloxy)ethyl]-2-propenoic acid as a colorless oily substance.

Quelle