Water → 4,4-Dimethyl-1-[2-(methylsulfonyl)benzyl]-2-(adamantan-2-yl)-1,2-diazetidin-3-one

HRID 888853Notes

Reaction equation

HRID 888853 reaction equation
[CH3:1][C:2]1([CH3:26])[N:5]([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[S:13][CH3:14])[N:4]([CH:15]2[CH:22]3[CH2:23][CH:18]4[CH2:19][CH:20]([CH2:24][CH:16]2[CH2:17]4)[CH2:21]3)[C:3]1=[O:25].[OH2:27].[OH:28]O.O>CO.[Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Ta+5]>[CH3:1][C:2]1([CH3:26])[N:5]([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[S:13]([CH3:14])(=[O:28])=[O:27])[N:4]([CH:15]2[CH:16]3[CH2:17][CH:18]4[CH2:19][CH:20]([CH2:21][CH:22]2[CH2:23]4)[CH2:24]3)[C:3]1=[O:25]

Participants

6

Reactant 3

HCID 962WaterHCID 449047Hydrogen peroxide waterHCID 673027144,4-Dimethyl-1-[2-(methylthio)benzyl]-2-(adamantan-2-yl)-1,2-diazetidin-3-one

Product 1

HCID 461959234,4-Dimethyl-1-[2-(methylsulfonyl)benzyl]-2-(adamantan-2-yl)-1,2-diazetidin-3-oneYield 32.1%

Reagents, catalysts & solvents 2

HCID 10269745Einecs 254-460-4CatalystHCID 887MethanolSolvent

Procedure

A solution of 4,4-dimethyl-1-[2-(methylthio)benzyl]-2-(adamantan-2-yl)-1,2-diazetidin-3-one (7.20 mg, 0.0186 mmol) prepared in Example 60 in methanol was added sequentially with tantalum pentachloride (3.30 mg, 0.00930 mmol) and hydrogen peroxide water (5.70 mg, 0.0558 mmol) at room temperature, and the resultant was stirred at the same temperature for 36.5 hours. The reaction solution was added with water and extracted with diethyl ether. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The obtained residue was purified using Preparative Thin-Layer chromatography (hexane:ethyl acetate=1:5), and the title compound (2.40 mg, 32.0%) was obtained as a white crystalline powder.

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe obtained residue was purified

Sources & evidence

ORD record
ord-cf646f32ff62497483ef5d8ec9c5e2d6
Source dataset
uspto-grants-2012_08
Patent number
US08252781B2

Reaction notes

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