2-Methyl-2-butene → HCID 69932982, compound

HRID 540769Notes

Reaction equation

HRID 540769 reaction equation
Cl([O-])=O.[Na+].[CH2:5]([N:7]1[C:11]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH:19]=[O:20])=[CH:15][CH:14]=2)=[CH:10][C:9]([C:21]2[CH:22]=[C:23]([C:27]([NH:30][S:31]([CH2:34][C:35]([F:38])([F:37])[F:36])(=[O:33])=[O:32])([CH3:29])[CH3:28])[CH:24]=[CH:25][CH:26]=2)=[N:8]1)[CH3:6].CC(=CC)C.P([O-])(O)(O)=[O:45].[Na+]>CO>[CH2:5]([N:7]1[C:11]([O:12][C:13]2[CH:14]=[CH:15][C:16]([C:19]([OH:45])=[O:20])=[CH:17][CH:18]=2)=[CH:10][C:9]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([CH3:29])([NH:30][S:31]([CH2:34][C:35]([F:38])([F:36])[F:37])(=[O:32])=[O:33])[CH3:28])[CH:22]=2)=[N:8]1)[CH3:6]

Participants

6

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 52913937HCID 52913937, compound

Product 1

HCID 69932982HCID 69932982, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium chlorite (71 mg, 0.78 mmol, 4.0 equiv) was added to a mixture of N-(1-{3-[1-ethyl-5-(4-formylphenoxy)-1H-pyrazol-3-yl]phenyl}-1-methylethyl)-2,2,2-trifluoroethanesulfonamide (97 mg, 0.20 mmol, 1 equiv), 2-methyl-2-butene (1 mL), aqueous sodium dihydrogenphosphate solution (20% w/w, 0.7 mL) and methanol (2.8 mL). The biphasic mixture was stirred for 90 minutes, then was partitioned between ethyl acetate and saturated aqueous sodium chloride solution. The organic layer was dried over sodium sulfate. The dried solution was filtered, and the filtrate was concentrated to afford 4-({1-ethyl-3-[3-(1-methyl-1-{[(2,2,2-trifluoroethyl)sulfonyl]amino}ethyl)phenyl]-1H-pyrazol-5-yl}oxy)benzoic acid. Calcd (M+1)+: 512.1. Found: 512.1.

Workup

  1. customwas partitioned between ethyl acetate and saturated aqueous sodium chloride solution
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationThe dried solution was filtered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f3c378e693234935b17078881130e890
Source dataset
uspto-grants-2014_10
Patent number
US08871796B2

Reaction notes

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