Benzyl 2,2,2-trichloroacetimidate → (3S)-3-(benzyloxy)butanoic acid ethyl ester

HRID 238943

Reaktionsgleichung

Reaktionsgleichung von HRID 238943
[CH2:1]([O:3][C:4](=[O:9])[CH2:5][C@@H:6]([OH:8])[CH3:7])[CH3:2].ClC(Cl)(Cl)C(=N)O[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(Cl)Cl.FC(F)(F)S(O)(=O)=O>[CH2:1]([O:3][C:4](=[O:9])[CH2:5][C@@H:6]([O:8][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:7])[CH3:2]

Komponenten

5

Edukt 2

HCID 144968Benzyl 2,2,2-trichloroacetimidateHCID 6950306Butanoic acid, 3-hydroxy-, ethyl ester, (3S)-

Produkt 1

HCID 14201835(3S)-3-(benzyloxy)butanoic acid ethyl esterAusbeute 200,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 62406Trifluoromethanesulfonic acidKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere, to a solution of (S)-(+)-3-hydroxybutyric acid ethyl ester (100 g, 0.76 mol) in methylene chloride (1.0 L), benzyl 2,2,2-trichloroacetoimidate (381 g, 1.5 mol) and trifluoromethanesulfonic acid (6.7 mL, 76 mmol) were gradually added, and the mixture was stirred at room temperature overnight. The precipitated solid was filtered, and after the mother liquid was successively washed with a saturated aqueous sodium hydrogencarbonate solution, water and saturated brine, it was dried with sodium sulfate and the solvent was distilled off under reduced pressure. Hexane was added to the residue, and after the solid was filtered again, the solvent of the mother liquid was distilled off under reduced pressure to give (3S)-3-(benzyloxy)butanoic acid ethyl ester (339 g) as a mixture. The present compound was used for the subsequent reaction without further purification.

Aufarbeitung

  1. filtrationThe precipitated solid was filtered
  2. washafter the mother liquid was successively washed with a saturated aqueous sodium hydrogencarbonate solution, water and saturated brine, it
  3. dry with materialwas dried with sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionHexane was added to the residue
  6. filtrationafter the solid was filtered again
  7. distillationthe solvent of the mother liquid was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8f6474ba20e846e49214da9fa1a069b8
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642640B2

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