Dichloromethane → N-(2,6-diisopropylphenyl)-2-[1-(4-methanesulfonyl-phenyl)-2,4-dioxo-1,3-diazaspiro[4.5]dec-3-yl]acetamide

HRID 1966960Notes

Reaction equation

HRID 1966960 reaction equation
O[O:2][S:3]([O-:5])=O.[K+].C([C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:19]3([CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[C:18](=[O:25])[N:17]([CH2:26][C:27]([NH:29][C:30]3[C:35]([CH:36]([CH3:38])[CH3:37])=[CH:34][CH:33]=[CH:32][C:31]=3[CH:39]([CH3:41])[CH3:40])=[O:28])[C:16]2=[O:42])=[CH:11][CH:10]=1)#N.Cl[CH2:44]Cl>CO.O>[CH:36]([C:35]1[CH:34]=[CH:33][CH:32]=[C:31]([CH:39]([CH3:41])[CH3:40])[C:30]=1[NH:29][C:27](=[O:28])[CH2:26][N:17]1[C:18](=[O:25])[C:19]2([CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[N:15]([C:12]2[CH:11]=[CH:10][C:9]([S:3]([CH3:44])(=[O:5])=[O:2])=[CH:14][CH:13]=2)[C:16]1=[O:42])([CH3:37])[CH3:38]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 23707502Potassium hydroxy sulfiteHCID 468924802-[1-(4-cyanophenyl)-2,4-dioxo-1,3-diaza-spiro[4.5]dec-3-yl]-N-(2,6-diisopropylphenyl)acetamide

Product 1

HCID 46892483N-(2,6-diisopropylphenyl)-2-[1-(4-methanesulfonyl-phenyl)-2,4-dioxo-1,3-diazaspiro[4.5]dec-3-yl]acetamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

0.421 g (0.684 mmol; 2.2 eq.) of oxone is added to a solution of 0.158 g (0.311 mmol; 1 eq.) of N-(2,6-diisopropylphenyl)-2-[1-(4-methylsulfanylphenyl)-2,4-dioxo-1,3-diazaspiro[4.5]dec-3-yl]acetamide (prepared according to Example 2) in 5 ml of methanol and 2 ml of demineralized water. The reaction medium is stirred at room temperature for 18 hours. Water and dichloromethane are added, and the organic phase is washed several times with water, dried over sodium sulfate and then concentrated to dryness. The product N-(2,6-diisopropylphenyl)-2-[1-(4-methanesulfonyl-phenyl)-2,4-dioxo-1,3-diazaspiro[4.5]dec-3-yl]acetamide is obtained in the form of a solid.

Workup

  1. washthe organic phase is washed several times with water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-45627f7dc80c46d09c41cf6f169bad0a
Source dataset
uspto-grants-2013_04
Patent number
US08420682B2

Reaction notes

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