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

HRID 604145Notes

Reaction equation

HRID 604145 reaction equation
[F:1][C:2]([F:43])([F:42])[C:3]1[CH:4]=[C:5]([CH:35]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:37]=1)[CH2:6][N:7]([CH2:13][C:14]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:15]=1[C:24]1[CH:29]=[C:28]([CH:30]([CH3:32])[CH3:31])[CH:27]=[CH:26][C:25]=1[O:33][CH3:34])[C:8]1[N:9]=[N:10][NH:11][N:12]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:63][S:64][CH2:65][CH2:66]O.N(C(OCC)=O)=NC(OCC)=O.C1(C)C=CC=CC=1>O1CCCC1.O>[F:41][C:38]([F:39])([F:40])[C:36]1[CH:35]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:42])[F:43])[CH:37]=1)[CH2:6][N:7]([CH2:13][C:14]1[CH:19]=[C:18]([C:20]([F:21])([F:22])[F:23])[CH:17]=[CH:16][C:15]=1[C:24]1[CH:29]=[C:28]([CH:30]([CH3:31])[CH3:32])[CH:27]=[CH:26][C:25]=1[O:33][CH3:34])[C:8]1[N:9]=[N:10][N:11]([CH2:66][CH2:65][S:64][CH3:63])[N:12]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 789252-(Methylthio)ethanolHCID 66777355Diethylazodicarboxylate tolueneHCID 86626888(3,5-bis-trifluoromethyl-benzyl)-(5'-isopropyl-2'-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-(2H-tetrazol-5-yl)-amine

Product 1

HCID 86626891(3,5-bis-trifluoromethyl-benzyl)-(5'-isopropyl-2'-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-[2-(2-methylsulfanyl-ethyl)-2H-tetrazol-5-yl]-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(3,5-Bis-trifluoromethyl-benzyl)-(5′-isopropyl-2′-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-(2H-tetrazol-5-yl)-amine (300 mg) is dissolved in tetrahydrofuran (5 ml) and thereto are added triphenylphosphine (191 mg), 2-(methylthio)ethanol (63 μl), a 40% diethyl azodicarboxylate/toluene solution (332 μl) and the mixture is stirred at room temperature for 2 hours and a half. To reaction mixture is added water and the mixture is extracted with diethylether. The organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=12:1) to give (3,5-bis-trifluoromethyl-benzyl)-(5′-isopropyl-2′-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-[2-(2-methylsulfanyl-ethyl)-2H-tetrazol-5-yl]-amine (270 mg). MS (m/z): 692 [M+H]+

Workup

  1. customTo reaction mixture
  2. extractionthe mixture is extracted with diethylether
  3. washThe organic layer is washed with a saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=12:1)

Sources & evidence

ORD record
ord-29558c18686945d78a48b64fcaecae5c
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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