m-Chloroperbenzoic acid → Methyl{[5'-isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}[(1-oxidopyridin-3-yl)methyl]carbamate

HRID 217523Notes

Reaction equation

HRID 217523 reaction equation
[CH3:1][O:2][C:3](=[O:34])[N:4]([CH2:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:14]=1[C:23]1[CH:28]=[C:27]([CH:29]([CH3:31])[CH3:30])[CH:26]=[CH:25][C:24]=1[O:32][CH3:33])[CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1.C1C=C(Cl)C=C(C(OO)=[O:43])C=1.OS([O-])=O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:34])[N:4]([CH2:12][C:13]1[CH:18]=[C:17]([C:19]([F:21])([F:22])[F:20])[CH:16]=[CH:15][C:14]=1[C:23]1[CH:28]=[C:27]([CH:29]([CH3:30])[CH3:31])[CH:26]=[CH:25][C:24]=1[O:32][CH3:33])[CH2:5][C:6]1[CH:7]=[N+:8]([O-:43])[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 23665763Sodium BisulfiteHCID 68690382Methyl{[5'-isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}(pyridin-3-ylmethyl)carbamate

Product 1

HCID 11533235Methyl{[5'-isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}[(1-oxidopyridin-3-yl)methyl]carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl{[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}(pyridin-3-ylmethyl)carbamate (12 mg, 0.025 mmol) (Example 123) in CH2Cl2 (400 μL) was added m-CPBA (28 mg, 0.13 mmol). The reaction was stirred at room temperature for two hours and then was poured into NaHSO3 (10 mL). The mixture was extracted with EtOAc (50 mL), and the organic extracts were washed with water (10 mL), brine (10 mL), dried over Na2SO4, filtered, and concentrated. Purification by flash chromatography with 10 to 20% MeOH/EtOAc afforded methyl{[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}[(1-oxidopyridin-3-yl)methyl]carbamate. Rf=0.36 (20% MeOH/EtOAc). LCMS=489.2 (M+1)+. 1H NMR (C6D6, 500 MHz, 70° C.) δ 6.21-8.22 (m, aromatics, 10H), 4.32 (s, 2H), 3.77 (s, 2H), 3.37 (s, 3H), 3.17 (s, 3H), 2.89 (m, 1H), 1.19 (d, J=7.0 Hz, 6H).

Workup

  1. extractionThe mixture was extracted with EtOAc (50 mL)
  2. washthe organic extracts were washed with water (10 mL), brine (10 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography with 10 to 20% MeOH/EtOAc

Sources & evidence

ORD record
ord-98d49c8a0fbb45b4adfd6a655d16802d
Source dataset
uspto-grants-2012_06
Patent number
US08193365B2

Reaction notes

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