Lithium Hydroxide → (2R,3S)-2-{[(tert-butoxy)carbonyl]amino}-3-methoxybutanoic acid

HRID 1792778Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1792778
C[O:2][C:3](=[O:17])[C@@H:4]([C@H:13]([CH3:16])[O:14][CH3:15])[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[Li+].[OH-]>O1CCOCC1.O>[C:6]([NH:5][C@@H:4]([C:3]([OH:17])=[O:2])[C@H:13]([CH3:16])[O:14][CH3:15])([O:8][C:9]([CH3:10])([CH3:12])[CH3:11])=[O:7]

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 23540192HCID 23540192, Verbindung

Produkt 1

HCID 23540191(2R,3S)-2-{[(tert-butoxy)carbonyl]amino}-3-methoxybutanoic acidAusbeute 90,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of N-Boc-O-methyl-D-threonine methyl ester (8.09 mmol) in 1,4-dioxane (10 mL) is added a solution of LiOH (24.3 mmol) in water (20 mL). After stirring for 2–3 h, the solvents are removed in vacuo and the residue partitioned between water and ether. The aqueous layer is acidified with solid citric acid to approximately pH 3, then extracted with ethyl acetate. The ethyl acetate extract is washed with water, dried with MgSO4, filtered and concentrated in vacuo to yield 1.70 g (90%) of the title compound.

Aufarbeitung

  1. customthe solvents are removed in vacuo
  2. customthe residue partitioned between water and ether
  3. extractionextracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. washis washed with water
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-dbaa94bd32244bae89e10ca244ba911a
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07078415B2

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