Hydrochloric Acid → HCID 90224810, compound

HRID 1487092Notes

Reaction equation

HRID 1487092 reaction equation
O1[C:5]2([CH2:10][CH2:9][N:8]([S:11](/[CH:14]=[CH:15]/[C:16]3[C:21]([CH3:22])=[CH:20][C:19]([N:23]4[C:27]([CH3:29])([CH3:28])[C:26](=[O:30])[NH:25][C:24]4=[O:31])=[CH:18][C:17]=3[CH3:32])(=[O:13])=[O:12])[CH2:7][CH2:6]2)[O:4]CC1.Cl.[OH-].[Na+]>O1CCCC1>[CH3:22][C:21]1[CH:20]=[C:19]([N:23]2[C:27]([CH3:28])([CH3:29])[C:26](=[O:30])[NH:25][C:24]2=[O:31])[CH:18]=[C:17]([CH3:32])[C:16]=1/[CH:15]=[CH:14]/[S:11]([N:8]1[CH2:7][CH2:6][C:5](=[O:4])[CH2:10][CH2:9]1)(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 90224866HCID 90224866, compound

Product 1

HCID 90224810HCID 90224810, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (E)-1-(4-(2-(1,4-dioxa-8-azaspiro[4.5]decan-8-ylsulfonyl)vinyl)-3,5-dimethylphenyl)-5,5-dimeth ylimidazolidine-2,4-dione (1.2 g, 2.58 mmol) in tetrahydrofuran (26 mL), a 2 N aqueous hydrochloric acid solution (26 mL, 52 mmol) was added dropwise over ten minutes. The mixture was stirred at 60° C. for two hours. The reaction mixture was cooled, followed by adjustment of its pH to 7 using a 2 N aqueous sodium hydroxide solution, and this mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane-ethyl acetate) to afford (E)-1-(3,5-dimethyl-4-(2-((4-oxopiperidin-1-yl)sulfonyl)vinyl)phenyl)-5,5-dimethylimidazolidine-2,4-dione (998 mg, 92%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionthis mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (dichloromethane-ethyl acetate)

Sources & evidence

ORD record
ord-77af8969286b446c91bc2e40fdf0a462
Source dataset
uspto-grants-2016_08
Patent number
US09428505B2

Reaction notes

Loading…