Potassium Hydroxide → (2R,3S)-2-benzyl-3-hydroxysuccinic acid

HRID 888212Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 888212
[CH2:1]([C@H:8]([C@H:15]([OH:22])[C:16]([O:18]C(C)C)=[O:17])[C:9]([O:11]C(C)C)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>O>[CH2:1]([C@H:8]([C@H:15]([OH:22])[C:16]([OH:18])=[O:17])[C:9]([OH:11])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 14797Potassium HydroxideHCID 14264444Diisopropyl (2R,3S)-2-benzyl-3-hydroxysuccinate

Produkt 1

HCID 54300227(2R,3S)-2-benzyl-3-hydroxysuccinic acidAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Diisopropyl (2R,3S)-2-benzyl-3-hydroxysuccinate (2.90 g; 15.9 mmol; 1.0 eq.) was taken in TIM (44 mL), cooled to 0° C. and was treated with KOH (3.17 g, 56.4 mmol) in water (14.5 mL). The resulting mixture was stirred at RT for 48 h. Tiff was removed and the residue was taken in water. The aqueous layer was washed with ether (100 mL) and was acidified with an aqueous solution of HCl (1.5 N), then was extracted with EtOAc. The combined organic layers were dried over Na2SO4 and then concentrated to give the title product as white solid (1.73 g, 82%).

Aufarbeitung

  1. customTiff was removed
  2. washThe aqueous layer was washed with ether (100 mL)
  3. extractionwas extracted with EtOAc
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-dec771f54c3142ba9523aff0a45e7bb5
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08247437B2

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