Potassium Persulfate → HCID 86751630, compound

HRID 2294682Notes

Reaction equation

HRID 2294682 reaction equation
CC[O-].[Na+].[CH2:5]([C:12](=[CH2:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:19][C:20](S)([CH3:30])[CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26].[S:32]([O:36]OS([O-])(=O)=O)([O-])(=O)=[O:33].[K+].[K+]>O1CCOCC1.O>[CH2:16]([O:15][C:13]([CH:12]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:18][S:32]([C:20]([CH3:30])([CH3:19])[CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:26])[CH3:28])(=[O:36])=[O:33])=[O:14])[CH3:17]

Participants

7

Reactant 4

HCID 24412Potassium Persulfate2×HCID 2723922Sodium ethoxideHCID 11084648Ethyl 2-benzylacrylateHCID 45092056HCID 45092056, compound

Product 1

HCID 86751630HCID 86751630, compoundYield 72.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 312751,4-DioxaneSolvent

Procedure

10.2 ml (11 mmol) of 1.08N sodium ethylate solution are added dropwise at 0° to a mixture of 1.99 g (10.47 mmol) of ethyl α-benzylacrylate and 2.26 g (11 mmol) of tert-butyl [2-methyl-2-mercaptopropyl]carbamate in 5 ml of dioxan. Thereafter, the mixture is stirred at 0° for 0.5 hours and at room temperature for 2.5 hours. The reaction mixture is treated while cooling with ice with 8.96 g (14.6 mmol) of potassium monopersulphate triple salt, suspended in 15 ml of water, and stirred at room temperature for 1 hour. Thereafter, the mixture is cooled to 0° and a suspension of 8.96 g (14.6 mmol) of potassium monopersulphate triple salt in 15 ml of water is again added. Subsequently, the mixture is stirred at room temperature for 15 hours. The reaction mixture is diluted with 50 ml of water and the aqueous solution is extracted three times with 50 ml of ether each time. The combined organic solutions are dried over sodium sulphate and evaporated. There are obtained 3.25 g of tert-butyl [2-[[(RS)-2-(ethoxycarbonyl)-3-phenylpropyl]sulphonyl]-2-methylpropyl]carbamate as a colourless oil; MS: 445 (M+NH4)+.

Workup

  1. additionThe reaction mixture is treated
  2. stirringstirred at room temperature for 1 hour
  3. temperatureThereafter, the mixture is cooled to 0°
  4. additionis again added
  5. stirringSubsequently, the mixture is stirred at room temperature for 15 hours
  6. extractionthe aqueous solution is extracted three times with 50 ml of ether each time
  7. dry with materialThe combined organic solutions are dried over sodium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-d1162822fc2c4c669138a4d4fe1c6555
Source dataset
uspto-grants-1997_11
Patent number
US05688946

Reaction notes

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