Hydrochloric Acid → HCID 118108867, compound

HRID 1508667Notes

Reaction equation

HRID 1508667 reaction equation
Cl.[CH3:2][S:3]([O:6][CH:7]([CH2:9][CH:10]([S:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)[CH:11]=NOC)[CH3:8])(=[O:5])=[O:4].C=[O:23]>CC(C)=O>[CH3:2][S:3]([O:6][CH:7]([CH2:9][CH:10]([S:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)[CH:11]=[O:23])[CH3:8])(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 118120842HCID 118120842, compound

Product 1

HCID 118108867HCID 118108867, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

14 mL of 2 mol/L hydrochloric acid was added to a mixture of 2.1 g of 5-(methoxyimino)-4-(pyridin-2-ylsulfanyl)pentan-2-yl methanesulfonate, 4.7 mL of a 36% formalin aqueous solution and 60 mL of acetone, and the obtained mixture was stirred at room temperature for 2 hours, and then at 50° C. for 3 hours. Thereafter, the solvent was distilled away under reduced pressure, 100 mL of ethyl acetate and 100 mL of water were then added to the residue, and the water layer was then removed. The organic layer was washed with a saturated sodium chloride aqueous solution, and was then dried over anhydrous magnesium sulfate. After that, the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/acetone=3/1), so as to obtain 0.90 g of 5-oxo-4-(pyridin-2-ylsulfanyl)pentan-2-yl methanesulfonate in the form of a colorless oily product.

Workup

  1. waitat 50° C. for 3 hours
  2. distillationThereafter, the solvent was distilled away under reduced pressure, 100 mL of ethyl acetate and 100 mL of water
  3. additionwere then added to the residue
  4. customthe water layer was then removed
  5. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  6. dry with materialwas then dried over anhydrous magnesium sulfate
  7. distillationAfter that, the solvent was distilled away under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (hexane/acetone=3/1)

Sources & evidence

ORD record
ord-88c842789bf140ff8608856b5cbdb0ef
Source dataset
uspto-grants-2015_12
Patent number
US09221865B2

Reaction notes

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