Lithium Hydroxide → (2E)-5-tert-Butoxycarbonylamino-3,5-dimethylhex-2-enoic acid

HRID 581199Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 581199
C([O:3][C:4](=[O:20])/[CH:5]=[C:6](\[CH3:19])/[CH2:7][C:8]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])([CH3:10])[CH3:9])C.[OH-].[Li+].COC(C)(C)C>O1CCOCC1.O.S([O-])(O)(=O)=O.[Na+]>[C:15]([O:14][C:12]([NH:11][C:8]([CH3:10])([CH3:9])[CH2:7]/[C:6](/[CH3:19])=[CH:5]/[C:4]([OH:20])=[O:3])=[O:13])([CH3:18])([CH3:16])[CH3:17]

Komponenten

7

Edukt 3

HCID 3939Lithium HydroxideHCID 15413tert-Butyl methyl etherHCID 10684548(E)-5-tert-Butoxycarbonylamino-3,5-dimethylhex-2-enoic acid ethylester

Produkt 1

HCID 10753633(2E)-5-tert-Butoxycarbonylamino-3,5-dimethylhex-2-enoic acidAusbeute 34,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 312751,4-DioxaneLösungsmittelHCID 516919Sodium BisulfateLösungsmittel

Versuchsvorschrift

(E)-5-tert-Butoxycarbonylamino-3,5-dimethylhex-2-enoic acid ethyl ester (1.95 g; 6.83 mmol) was dissolved in 1,4-dioxane (25 ml) and water (15 ml). Lithium hydroxide (0.18 g; 7.52 mmol) was added and the reaction mixture was stirred for 12 h at room temperature. Water (150 ml) and tert-butyl methyl ether (150 ml) was added. The aqueous phase was diluted with an aqueous solution of sodium hydrogensulfate (10%) until pH 2.5 and extracted with tert-butyl methyl ether (3×100 ml). The combined organic phases were dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from heptane (20 ml) to afford 0.6 g of (2E)-5-tert-butoxycarbonylamino-3,5-dimethylhex-2-enoic acid.

Aufarbeitung

  1. extractionextracted with tert-butyl methyl ether (3×100 ml)
  2. dry with materialThe combined organic phases were dried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was recrystallized from heptane (20 ml)

Quellen und Nachweise

ORD-Eintrag
ord-6d7d2ec579454b379a5b7061e56e6bf5
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05919777

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