Hydrochloric Acid → HCID 23070878, compound

HRID 501393Notes

Reaction equation

HRID 501393 reaction equation
Cl.[CH2:2]([N:6]1[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:9]([C:16]([S:18][CH3:19])=N)[N:8]=[C:7]1[N:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]1)[C:3]#[C:4][CH3:5].C([OH:35])C>>[CH2:2]([N:6]1[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:9]([C:16]([S:18][CH3:19])=[O:35])[N:8]=[C:7]1[N:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:31])([CH3:32])[CH3:30])=[O:27])[CH2:22][CH2:21]1)[C:3]#[C:4][CH3:5]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 23070735HCID 23070735, compound

Product 1

HCID 23070878HCID 23070878, compound

Conditions

Temperature
60 °C

Procedure

5 ml of a 2N aqueous solution of hydrochloric acid was added to a 30-ml ethanol solution of 0.55 g of t-butyl 4-[1-(2-butynyl)-5-ethoxycarbonyl-4-methyl sulfanylcarbonimidoyl-1H-imidazol-2-yl]piperazine-1-carboxylate, and the mixture was heated at 60° C. for 5 hours. After the reaction solution had been concentrated under reduced pressure, 25 ml of ethyl acetate and 1N sodium hydroxide solution were added thereto. The aqueous layer was extracted with 25 ml of ethyl acetate, and the organic layers were combined together. The mixture was washed with 10 ml of a saturated sodium chloride solution containing 1 ml of 1N sodium hydroxide solution, and dried over anhydrous magnesium sulfate. The solution was filtered, and the filtrate was concentrated under reduced pressure. The residue was dissolved in 10 ml of dichloromethane, and 0.10 ml of triethylamine and 0.256 g of di-t-butyl dicarbonate were added thereto. The mixture was stirred at room temperature for 15 hours, and then 25 ml of ethyl acetate was added thereto. The mixture was washed successively with 10 ml of 0.1N hydrochloric acid, 10 ml of a saturated sodium bicarbonate solution, and 10 ml of a saturated sodium chloride solution, and then dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography. Thus, 0.15 g of the title compound was obtained from the fraction eluted with hexane-ethyl acetate (4:1).

Workup

  1. concentrationAfter the reaction solution had been concentrated under reduced pressure, 25 ml of ethyl acetate and 1N sodium hydroxide solution
  2. additionwere added
  3. extractionThe aqueous layer was extracted with 25 ml of ethyl acetate
  4. washThe mixture was washed with 10 ml of a saturated sodium chloride solution
  5. additioncontaining 1 ml of 1N sodium hydroxide solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe solution was filtered
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. dissolutionThe residue was dissolved in 10 ml of dichloromethane
  10. addition0.10 ml of triethylamine and 0.256 g of di-t-butyl dicarbonate were added
  11. addition25 ml of ethyl acetate was added
  12. washThe mixture was washed successively with 10 ml of 0.1N hydrochloric acid, 10 ml of a saturated sodium bicarbonate solution, and 10 ml of a saturated sodium chloride solution
  13. dry with materialdried over anhydrous magnesium sulfate
  14. concentrationThe solution was concentrated under reduced pressure
  15. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5fa65d6db5b74f9b9f5eb3befe347aab
Source dataset
uspto-grants-2010_08
Patent number
US07772226B2

Reaction notes

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