Lithium Hydroxide → HCID 4712492, compound

HRID 1167388Notes

Reaction equation

HRID 1167388 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:15][C:16]([CH3:18])=[CH2:17])[C:10]([O:12]CC)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-]>CC(C)=O>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:15][C:16]([CH3:18])=[CH2:17])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 15674243HCID 15674243, compound

Product 1

HCID 4712492HCID 4712492, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of ethyl (2RS)-2-tert-butoxycarbonylamino-4-methyl-4-pentenoate EXAMPLE 1.C, above (6.9 g, 26.9 mmol) in acetone (50 mL was added LiOH (108 mL of 1 N aqueous solution, 108 mmol). The clear solution was stirred at room temperature for 0.5 hour. Acetone was evaporated under reduced pressure, the pH of the resulting aqueous solution was then adjusted to 3 by addition of 1 N HCl and the aqueous layer was extracted with EA (3×50 mL). The organic layers were combined, washed with brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to give the desired acid as a pale yellow oil in quantitative yield.

Workup

  1. customAcetone was evaporated under reduced pressure
  2. additionthe pH of the resulting aqueous solution was then adjusted to 3 by addition of 1 N HCl
  3. extractionthe aqueous layer was extracted with EA (3×50 mL)
  4. washwashed with brine (50 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-16ba92ed7292411b95490be033a525d0
Source dataset
uspto-grants-2003_09
Patent number
US06617426B1

Reaction notes

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