Lithium Hydroxide → (S)-3-hydroxy-3-[2-(4-hydroxy-phenyl)-ethyl]4-methyl-pentanoic acid

HRID 1003883Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1003883
C[O:2][C:3](=[O:19])[CH2:4][C@@:5]([OH:18])([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[CH:6]([CH3:8])[CH3:7].[OH-].[Li+]>CO.O>[OH:18][C@:5]([CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=1)([CH:6]([CH3:7])[CH3:8])[CH2:4][C:3]([OH:19])=[O:2]

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 53666244(S)-3-Hydroxy-3-[2-(4-hydroxy-phenyl)-ethyl]-4-methyl-pentanoic acid methyl ester

Produkt 1

HCID 53816519(S)-3-hydroxy-3-[2-(4-hydroxy-phenyl)-ethyl]4-methyl-pentanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

The title compound was prepared by dissolving (S)-3-hydroxy-3-[2-(4-hydroxy-phenyl)-ethyl]-4-methyl-pentanoic acid methyl ester (0.57 g, 2.15 mmol) from Example TTTT in MeOH (30 mL). Lithium hydroxide (0.18 g, 4.29 mmol) in water (10 mL) was added and the reaction heated to reflux for 1 hour, cooled and pumped to dryness under vacuum. The product was partitioned between water and Et2O. The aqueous layer was decanted, acidified with 1N HCl and extracted with Et2O. The solution was dried (MgSO4) and concentrated to give the title compound (m.p. 137-140° C.).

Aufarbeitung

  1. customThe title compound was prepared
  2. temperaturethe reaction heated
  3. temperatureto reflux for 1 hour
  4. temperaturecooled
  5. customThe product was partitioned between water and Et2O
  6. customThe aqueous layer was decanted
  7. extractionextracted with Et2O
  8. dry with materialThe solution was dried (MgSO4)
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-637a6e81307244d3a72e9f43563fbdea
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06046355

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