Acetic Acid → HCID 23070638, compound

HRID 501430Notes

Reaction equation

HRID 501430 reaction equation
[C-]#N.[Na+].C(O)(=O)C.[C:8](#[N:10])C.[CH2:11]([N:15]1[C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([CH:24]=[O:25])[N:17]=[C:16]1[N:26]1[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]1)[C:12]#[C:13][CH3:14]>C(OCC)(=O)C>[CH2:11]([N:15]1[C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([CH:24]([C:8]#[N:10])[OH:25])[N:17]=[C:16]1[N:26]1[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]1)[C:12]#[C:13][CH3:14]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6342AcetonitrileHCID 8929Sodium CyanideHCID 23070919HCID 23070919, compound

Product 1

HCID 23070638HCID 23070638, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

0.200 g of sodium cyanide and 0.010 ml of acetic acid were added to a 15 ml acetonitrile solution of t-butyl 4-[1-(2-butynyl)-5-methoxycarbonyl-4-formyl-1H-imidazol-2-yl]piperazine-1-carboxylate, and the mixture was stirred at room temperature for 16 hours. 100 ml of ethyl acetate was added to the solution, and the mixture was washed twice with 50 ml of water and then with 50 ml of a saturated sodium chloride solution. The organic layer was dried over magnesium sulfate, and the solvent was concentrated under reduced pressure. The residue was purified by silica gel column chromatography. Thus, 0.274 g of the title compound was obtained from the fraction eluted with ethyl acetate-hexane (2:3).

Workup

  1. washthe mixture was washed twice with 50 ml of water
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationthe solvent was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0731fbf88cce487f9b92d25381dbc471
Source dataset
uspto-grants-2010_08
Patent number
US07772226B2

Reaction notes

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