m-Chloroperbenzoic acid → (3,5-bis-trifluoromethyl-benzyl)-(5'-isopropyl-2'-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-[2-(2-methanesulfonyl-ethyl)-2H-tetrazol-5-yl]-amine

HRID 658079Notes

Reaction equation

HRID 658079 reaction equation
[F:1][C:2]([F:48])([F:47])[C:3]1[CH:4]=[C:5]([CH:40]=[C:41]([C:43]([F:46])([F:45])[F:44])[CH:42]=1)[CH2:6][N:7]([CH2:18][C:19]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:20]=1[C:29]1[CH:34]=[C:33]([CH:35]([CH3:37])[CH3:36])[CH:32]=[CH:31][C:30]=1[O:38][CH3:39])[C:8]1[N:9]=[N:10][N:11]([CH2:13][CH2:14][S:15]([CH3:17])=[O:16])[N:12]=1.ClC1C=CC=C(C(OO)=[O:57])C=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[F:44][C:43]([F:46])([F:45])[C:41]1[CH:40]=[C:5]([CH:4]=[C:3]([C:2]([F:47])([F:1])[F:48])[CH:42]=1)[CH2:6][N:7]([CH2:18][C:19]1[CH:24]=[C:23]([C:25]([F:26])([F:27])[F:28])[CH:22]=[CH:21][C:20]=1[C:29]1[CH:34]=[C:33]([CH:35]([CH3:36])[CH3:37])[CH:32]=[CH:31][C:30]=1[O:38][CH3:39])[C:8]1[N:9]=[N:10][N:11]([CH2:13][CH2:14][S:15]([CH3:17])(=[O:57])=[O:16])[N:12]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 86626892(3,5-bis-trifluoromethyl-benzyl)-(5'-isopropyl-2'-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-[2-(2-methanesulfinyl-ethyl)-2H-tetrazol-5-yl]-amine

Product 1

HCID 86626903(3,5-bis-trifluoromethyl-benzyl)-(5'-isopropyl-2'-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-[2-(2-methanesulfonyl-ethyl)-2H-tetrazol-5-yl]-amineYield 61.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

(3,5-Bis-trifluoromethyl-benzyl)-(5′-isopropyl-2′-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-[2-(2-methanesulfinyl-ethyl)-2H-tetrazol-5-yl]-amine (129 mg) is dissolved in chloroform (2 ml), and thereto is added m-chloroperbenzoic acid (50 mg) and the mixture is stirred at room temperature overnight. To the reaction solution is added a saturated aqueous sodium bicarbonate solution, and the mixture is extracted with ethyl acetate, and the organic layer is washed with a brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give (3,5-bis-trifluoromethyl-benzyl)-(5′-isopropyl-2′-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-[2-(2-methanesulfonyl-ethyl)-2H-tetrazol-5-yl]-amine (81 mg). MS (m/z): 724 [M+H]+

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washthe organic layer is washed with a brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-cf15e8725d2a4359b18c816ff41f433d
Source dataset
uspto-grants-2011_12
Patent number
US08076364B2

Reaction notes

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