Hydrogen Peroxide → HCID 66817822, compound

HRID 1755089Notes

Reaction equation

HRID 1755089 reaction equation
[OH:1]O.[CH3:3][C:4]1[CH:5]=[C:6]([N:36]([CH3:40])[C:37]([NH2:39])=[O:38])[CH:7]=[C:8]([CH3:35])[C:9]=1/[CH:10]=[CH:11]/[S:12]([N:15]1[CH2:34][CH2:33][C:18]2([N:22]=[C:21]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][S:28][CH2:29][CH2:30][CH3:31])[NH:20][C:19]2=[O:32])[CH2:17][CH2:16]1)(=[O:14])=[O:13].O>CC(C)=O>[CH3:35][C:8]1[CH:7]=[C:6]([N:36]([CH3:40])[C:37]([NH2:39])=[O:38])[CH:5]=[C:4]([CH3:3])[C:9]=1/[CH:10]=[CH:11]/[S:12]([N:15]1[CH2:16][CH2:17][C:18]2([N:22]=[C:21]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][S:28]([CH2:29][CH2:30][CH3:31])=[O:1])[NH:20][C:19]2=[O:32])[CH2:33][CH2:34]1)(=[O:13])=[O:14]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 962WaterHCID 66816856HCID 66816856, compound

Product 1

HCID 66817822HCID 66817822, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

30% aqueous hydrogen peroxide (0.013 ml) was added to a mixed solution of (E)-1-(3,5-dimethyl-4-(2-((4-oxo-2-(5-(propylthio)pentyl)-1,3,8-triazaspiro[4.5]dec-1-en-8-yl)sulfonyl)vinyl)phenyl)-1-methyl-urea (55 mg) and molybdenum(IV) dichloride dioxide (3 mg) in acetone (1.5 ml)-water (0.5 ml), and the mixture was stirred at room temperature for five minutes in a nitrogen stream. The reaction mixture was quenched with a saturated aqueous sodium bicarbonate solution and then extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting residue was purified by column chromatography (silica gel, CH2Cl2-MeOH) to give 1-[3,5-dimethyl-4-((E)-2-{4-oxo-2-[5-(propane-1-sulfinyl)-pentyl]-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl}-vinyl)-phenyl]-1-methyl-urea (64 mg).

Workup

  1. customThe reaction mixture was quenched with a saturated aqueous sodium bicarbonate solution
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by column chromatography (silica gel, CH2Cl2-MeOH)

Sources & evidence

ORD record
ord-13fd3938f68e41749b8543955225f833
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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