Sodium Hydroxide → HCID 23070604, compound

HRID 501447Notes

Reaction equation

HRID 501447 reaction equation
[OH-].[Na+].[CH2:3]([N:7]1[C:11]([C:12]#[N:13])=[C:10]([C:14]([O:16]CC)=[O:15])[N:9]=[C:8]1[N:19]1[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]1)[C:4]#[C:5][CH3:6]>C(O)C>[CH2:3]([N:7]1[C:11]([C:12]#[N:13])=[C:10]([C:14]([OH:16])=[O:15])[N:9]=[C:8]1[N:19]1[CH2:20][CH2:21][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:23][CH2:24]1)[C:4]#[C:5][CH3:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23070704HCID 23070704, compound

Product 1

HCID 23070604HCID 23070604, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

16 ml of a 5N aqueous sodium hydroxide solution was added to a 500 ml ethanol solution of 25.1 g of t-butyl 4-[1-(2-butynyl)-5-cyano-4-ethoxycarbonyl-1H-imidazol-2-yl]piper azine-1-carboxylate, and the mixture was stirred at room temperature for two hours. Then, the solvent was concentrated under reduced pressure. The residue was dissolved in a mixture consisting of 1 L of ethyl acetate and 500 ml of water. 50 ml of 2N hydrochloric acid was added to the solution. The organic layer was washed with 200 ml of a saturated sodium chloride solution, and dried over magnesium sulfate. The organic liquid was concentrated under reduced pressure to give 23.2 g of the title compound.

Workup

  1. concentrationThen, the solvent was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in a mixture
  3. addition50 ml of 2N hydrochloric acid was added to the solution
  4. washThe organic layer was washed with 200 ml of a saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe organic liquid was concentrated under reduced pressure

Sources & evidence

ORD record
ord-64513e9202094af8982175800a5ae2c9
Source dataset
uspto-grants-2010_08
Patent number
US07772226B2

Reaction notes

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