Hydrogen Peroxide → HCID 135961987, compound

HRID 2233584Notes

Reaction equation

HRID 2233584 reaction equation
[CH2:1]([C:5]1[N:6]=[C:7]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)[S:8][C:9]=1[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[NH:22][C:21](=[O:23])[O:20][N:19]=2)=[C:14]([Cl:24])[CH:13]=1)[CH2:2][CH:3]=[CH2:4].[OH-:35].[Na+].OO.O>O1CCCC1>[Cl:24][C:14]1[CH:13]=[C:12]([O:11][CH2:10][C:9]2[S:8][C:7]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:33])([F:32])[F:34])=[CH:27][CH:26]=3)=[N:6][C:5]=2[CH2:1][CH2:2][CH2:3][CH2:4][OH:35])[CH:17]=[CH:16][C:15]=1[C:18]1[NH:22][C:21](=[O:23])[O:20][N:19]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 135961981HCID 135961981, compound

Product 1

HCID 135961987HCID 135961987, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 50 mg of 3-{4-[4-but-3-enyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-chloro-phenyl}-4H-[1,2,4]oxadiazol-5-one in 2 ml of tetrahydrofuran at 0° C. was added 0.3 ml of a 2M solution of borane-methylsulfide complex in tetrahydrofuran. The resulting mixture was stirred allowing it to warm up to room temperature than stirred at room temperature for 30 minutes. After cooling to 0° C., 0.1 ml of a 5M aqueous solution of sodium hydroxide and 0.1 ml of a 30% aqueous solution of hydrogen peroxide were added. The resulting mixture was stirred allowing it to warm up to room temperature over 1 hour. It was then poured into water, extracted with ethyl acetate, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (gradient of dichloromethane/methanol from 100/0 to 95/5) followed by crystallization from dichloromethane/pentane to give 28 mg of 3-{2-chloro-4-[4-(4-hydroxy-butyl)-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-4H-[1,2,4]oxadiazol-5-one.

Workup

  1. stirringthan stirred at room temperature for 30 minutes
  2. temperatureAfter cooling to 0° C.
  3. stirringThe resulting mixture was stirred
  4. temperatureto warm up to room temperature over 1 hour
  5. extractionextracted with ethyl acetate
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified by column chromatography on silica gel (gradient of dichloromethane/methanol from 100/0 to 95/5)
  10. customfollowed by crystallization from dichloromethane/pentane

Sources & evidence

ORD record
ord-58c5e5eb5e8541a2918ba41a3513fc9c
Source dataset
uspto-grants-2010_05
Patent number
US07709509B2

Reaction notes

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