Hydrogen Peroxide → HCID 67466380, compound

HRID 1845914Notes

Reaction equation

HRID 1845914 reaction equation
[F:1][C:2]1([F:25])[CH2:4][CH:3]1[CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][C:13](B3OC(C)(C)C(C)(C)O3)=[CH:14][C:9]=2[S:8][C:7]1=[O:24].[OH:26]O>O1CCOCC1.O.CO.CN1C(=O)CCC1>[F:1][C:2]1([F:25])[CH2:4][CH:3]1[CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][C:13]([OH:26])=[CH:14][C:9]=2[S:8][C:7]1=[O:24]

Participants

7

Reactant 2

HCID 784Hydrogen PeroxideHCID 70170320HCID 70170320, compound

Product 1

HCID 67466380HCID 67466380, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-[(2,2-difluorocyclopropyl)methyl]-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-benzothiazol-2(3H)-one (18-1) (0.483 g, 1.32 mmol) in anhydrous 1,4-dioxane (5 mL) was added a 30% by weight solution of hydrogen peroxide in water (0.537 mL, 5.26 mmol. The reaction mixture was then stirred at room temperature for 0.5 hours. The crude reaction mixture was diluted with methanol and NMP, filtered and concentrated. Purification of crude reaction mixture by reverse phase chromatography (Waters Sunfire MSC18, 5% acetonitrile/0.1% trifluoroacetic acid/water→95% acetonitrile/0.1% trifluoroacetic acid/water) gave 3-[2,2-difluorocyclopropyl)methyl]-6-hydroxy-1,3-benzothiazol-2(3H)-one (18-2) as a tan solid. HRMS (M+H)+: observed=258.0396, calculated=258.0395.

Workup

  1. customThe crude reaction mixture
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customPurification of crude
  5. customreaction mixture by reverse phase chromatography (Waters Sunfire MSC18, 5% acetonitrile/0.1% trifluoroacetic acid/water→95% acetonitrile/0.1% trifluoroacetic acid/water)

Sources & evidence

ORD record
ord-d01602dedda34954830731c2d1ae0c61
Source dataset
uspto-grants-2015_02
Patent number
US08952005B2

Reaction notes

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