Hydrochloric Acid → HCID 23070903, compound

HRID 501394Notes

Reaction equation

HRID 501394 reaction equation
[BH4-].[Na+].C(O)C.[CH2:6]([N:10]1[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:13]([C:20](SC)=[O:21])[N:12]=[C:11]1[N:24]1[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]1)[C:7]#[C:8][CH3:9].Cl>C([O-])(=O)C.[Hg+2].C([O-])(=O)C.C(OCC)(=O)C>[CH2:6]([N:10]1[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:13]([CH2:20][OH:21])[N:12]=[C:11]1[N:24]1[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:34])([CH3:36])[CH3:35])=[O:31])[CH2:26][CH2:25]1)[C:7]#[C:8][CH3:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 4311764Sodium borohydride2×HCID 23070878HCID 23070878, compound

Product 1

HCID 23070903HCID 23070903, compoundYield 25.5%

Reagents, catalysts & solvents 2

HCID 15337Mercuric acetateCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

0.187 g of mercury (II) acetate and 0.090 of sodium borohydride were added to 8 ml of an ethanol solution containing 0.265 g of t-butyl 4-[1-(2-butynyl)-5-ethoxycarbonyl-4-methylsulfanyl carbonyl-1H-imidazol-2-yl]piperazine-1-carboxylate at 0° C., and the mixture was stirred at room temperature for 4 hours. After 0.187 g of mercury (II) acetate and 0.090 of sodium borohydride had been added to the solution, the mixture was stirred at room temperature for 15 hours. 100 ml of ethyl acetate and 50 ml of 0.5N hydrochloric acid were added to the solution, and the organic layer was washed successively with 50 ml of water and 50 ml of a saturated sodium chloride solution. The mixture was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography. 0.172 g of the starting material was collected from the fraction eluted with hexane-ethyl acetate (4:1). Then, 0.061 g of the title compound was obtained from the fraction eluted with hexane-ethyl acetate (1:4).

Workup

  1. stirringthe mixture was stirred at room temperature for 15 hours
  2. washthe organic layer was washed successively with 50 ml of water and 50 ml of a saturated sodium chloride solution
  3. dry with materialThe mixture was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography
  6. custom0.172 g of the starting material was collected from the fraction
  7. washeluted with hexane-ethyl acetate (4:1)

Sources & evidence

ORD record
ord-aee4171ffd7f47a6ae020a6bd65b03f3
Source dataset
uspto-grants-2010_08
Patent number
US07772226B2

Reaction notes

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