Lithium Hydroxide → (S)-2-((t-Butoxycarbonyl)amino)-3-(tetrahydro-2H-pyran-4-yl)propanoic acid

HRID 1972340Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1972340
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([O:19]C)=[O:18])[CH2:10][CH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1COCC1.[OH-].[Li+]>O>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([OH:19])=[O:18])[CH2:10][CH:11]1[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 29947234methyl N-(tert-butoxycarbonyl)-3-(tetrahydro-2H-pyran-4-yl)-L-alaninate

Produkt 1

HCID 7168106(S)-2-((t-Butoxycarbonyl)amino)-3-(tetrahydro-2H-pyran-4-yl)propanoic acidAusbeute 95,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A 500-mL round-bottomed flask was charged with methyl N-(tert-butoxycarbonyl)-3-(tetrahydro-2H-pyran-4-yl)-L-alaninate (8.81 g, 30.7 mmol), 100 mL of THF, 100 mL of water and lithium hydroxide (2.20 g, 92 mmol). After stirring overnight at room temperature, the mixture was concentrated and acidified to pH 3 with concentrated aqueous HCl. The mixture was then extracted with EtOAc, dried (MgSO4), filtered, and concentrated to give N-(tert-butoxycarbonyl)-3-(tetrahydro-2H-pyran-4-yl)-L-alanine (8.00 g) as a white solid.

Aufarbeitung

  1. concentrationthe mixture was concentrated
  2. extractionThe mixture was then extracted with EtOAc
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d3a7818135f74daaa54d455a12ca3682
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08431563B2

Notizen zur Reaktion

Wird geladen…