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

HRID 2104316Notes

Reaction equation

HRID 2104316 reaction equation
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]

Participants

7

Reactant 3

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

Product 1

HCID 10753633(2E)-5-tert-Butoxycarbonylamino-3,5-dimethylhex-2-enoic acidYield 34.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolventHCID 516919Sodium BisulfateSolvent

Procedure

(2E)-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 a 10% aqueous solution of sodium hydrogensulfate until pH 25 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.

Workup

  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)

Sources & evidence

ORD record
ord-063ab1c3f88a4edfb656c80c316c8c26
Source dataset
uspto-grants-2009_08
Patent number
US07576062B2

Reaction notes

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