m-Chloroperbenzoic acid → HCID 86649770, compound

HRID 1880253Notes

Reaction equation

HRID 1880253 reaction equation
[F:1][C:2]([F:41])([F:40])[C:3]1[CH:4]=[C:5]([C:13]2([C:36]([F:39])([F:38])[F:37])[O:17][N:16]=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][NH:25][C:26](=[O:34])[CH:27]([S:31][CH2:32][CH3:33])[S:28][CH2:29][CH3:30])=[C:20]([Cl:35])[CH:19]=3)[CH2:14]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.ClC1C=CC=C(C(OO)=[O:50])C=1.S([O-])(O)=O.[Na+]>ClCCl>[F:10][C:9]([F:12])([F:11])[C:7]1[CH:6]=[C:5]([C:13]2([C:36]([F:38])([F:37])[F:39])[O:17][N:16]=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][NH:25][C:26](=[O:34])[CH:27]([S:28]([CH2:29][CH3:30])=[O:50])[S:31][CH2:32][CH3:33])=[C:20]([Cl:35])[CH:19]=3)[CH2:14]2)[CH:4]=[C:3]([C:2]([F:40])([F:1])[F:41])[CH:8]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 23665763Sodium BisulfiteHCID 86649771HCID 86649771, compound

Product 1

HCID 86649770HCID 86649770, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.37 g of N-[4-[5-[3,5-bis(trifluoromethyl)phenyl]-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-chlorophenyl]methyl-2,2-bis(ethylthio) acetamide (compound of the present invention No. 1-215) in 5 mL of dichloromethane, 0.098 g of 3-chloroperbenzoic acid (75%) was added while stirring the solution at room temperature and the resultant reaction mixture was stirred at the same temperature for 1 hour. After the completion of the reaction, 5 mL of a saturated sodium hydrogen sulfite aqueous solution was added to the reaction mixture and the resultant mixture was extracted with dichloromethane (5 mL×2). The organic phase was washed with water and then dehydrated and dried over saturated saline and anhydrous magnesium sulfate in this order and the solvent was distilled off under reduced pressure. The resultant residue was purified by preparative medium pressure liquid chromatography eluting with ethyl acetate-hexane (a gradient from 1:1 to 1:5) using a medium pressure preparative apparatus (trade name: YFLC-Wprep; manufactured by Yamazen Corporation) to obtain 0.282 g of the objective substance as a colorless resinoid.

Workup

  1. customthe resultant reaction mixture
  2. stirringwas stirred at the same temperature for 1 hour
  3. additionwas added to the reaction mixture
  4. extractionthe resultant mixture was extracted with dichloromethane (5 mL×2)
  5. washThe organic phase was washed with water
  6. dry with materialdried over saturated saline and anhydrous magnesium sulfate in this order
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe resultant residue was purified by preparative medium pressure liquid chromatography
  9. washeluting with ethyl acetate-hexane (a gradient from 1:1 to 1:5)
  10. customto obtain 0.282 g of the objective substance as a colorless resinoid

Sources & evidence

ORD record
ord-5918d2c3f0174d34a97575e69308d3bd
Source dataset
uspto-grants-2012_11
Patent number
US08318757B2

Reaction notes

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