Ammonia → HCID 23070753, compound

HRID 501431Notes

Reaction equation

HRID 501431 reaction equation
OO.N.[CH2:4]([N:8]1[C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([CH:17]([C:19]#[N:20])[OH:18])[N:10]=[C:9]1[N:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]1)[C:5]#[C:6][CH3:7].S([O-])(O)=[O:35].[Na+]>CO>[CH2:4]([N:8]1[C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([CH:17]([C:19](=[O:35])[NH2:20])[OH:18])[N:10]=[C:9]1[N:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]1)[C:5]#[C:6][CH3:7]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 784Hydrogen PeroxideHCID 23070638HCID 23070638, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 23070753HCID 23070753, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.2 ml of 30% aqueous hydrogen peroxide and 3.2 ml of 28% aqueous ammonia solution were added to an 8 ml methanol solution of 0.274 g of t-butyl 4-[1-(2-butynyl)-4-(cyano-hydroxymethyl)-5-methoxycarbonyl-1H-imidazol-2-yl]piperazine-1-carboxylate at 5° C., and the mixture was stirred for 15 hours. 100 ml of a saturated sodium hydrogen sulfite solution was added to the solution, and the mixture was extracted twice with 100 ml of ethyl acetate. The organic layers were combined together. The combined organic layers were dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography. Thus, 0.039 g of the title compound was obtained from the fraction eluted with methanol-ethyl acetate (1:9).

Workup

  1. extractionthe mixture was extracted twice with 100 ml of ethyl acetate
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bb94ce777b294ae69c66b8c130d255d9
Source dataset
uspto-grants-2010_08
Patent number
US07772226B2

Reaction notes

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