m-Chloroperbenzoic acid → HCID 11707037, compound

HRID 217521Notes

Reaction equation

HRID 217521 reaction equation
[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([O:39][CH3:40])=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=2[CH2:20][N:21]([CH2:26][C:27]2[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[C:29]([S:37][CH3:38])[CH:28]=2)[C:22](=[O:25])[O:23][CH3:24])[CH:9]=1)([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:49])C=1.OS([O-])=O.[Na+]>C(Cl)Cl>[CH3:24][O:23][C:22](=[O:25])[N:21]([CH2:20][C:11]1[CH:12]=[C:13]([C:16]([F:18])([F:19])[F:17])[CH:14]=[CH:15][C:10]=1[C:8]1[CH:9]=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:5]=[CH:6][C:7]=1[O:39][CH3:40])[CH2:26][C:27]1[CH:32]=[C:31]([C:33]([F:35])([F:36])[F:34])[CH:30]=[C:29]([S:37]([CH3:38])=[O:49])[CH:28]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 23665763Sodium BisulfiteHCID 86615396HCID 86615396, compound

Product 1

HCID 11707037HCID 11707037, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Methyl {[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}[3-(methylthio)-5-(trifluoromethyl)benzyl]carbamate (21.7 mg, 0.037 mmol) (Example 129) in CH2Cl2 (1 mL) was cooled to −78° C. Next, m-CPBA (8.3 mg, 0.037 mmol) was added. The reaction was stirred at −78° C. for fifteen minutes, then was warmed to −45° C., and after five minutes at −45° C. was poured into NaHSO3 (10 mL). The mixture was extracted with EtOAc (50 mL), and the organic extracts were washed with water (10mL), brine (10 mL), dried over Na2SO4, filtered, and concentrated. Purification by flash chromatography with 50% EtOAc/hexanes afforded methyl{[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}[3-(methylsulfinyl)-5-(trifluoromethyl)benzyl]carbamate. Rf=0.20 (50% EtOAc/hexanes). LCMS=602.2 (M+1)+.1H NMR (C6D6, 500 MHz, 70° C.) δ 7.63 (broad singlet, 1H), 7.54 (broad singlet, 1H), 7.48 (broad singlet, 1H), 7.33 (s, 1H), 7.32 (s, 1H), 7.07-7.05 (m, 2H), 6.89 (s, 1H), 6.62 (d, J=8.0 Hz, 1H), 4.41 (broad singlet, 2H), 4.04 (broad singlet, 2H), 3.37 (s, 3H), 3.30 (s, 3H), 2.75 (m, 1H), 1.93 (s, 3H), 1.16 (d, J=6.5 Hz, 6H).

Workup

  1. temperaturewas warmed to −45° C.
  2. extractionThe mixture was extracted with EtOAc (50 mL)
  3. washthe organic extracts were washed with water (10mL), brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography with 50% EtOAc/hexanes

Sources & evidence

ORD record
ord-7de5f72eec10484cadc2808069f1ec88
Source dataset
uspto-grants-2012_06
Patent number
US08193365B2

Reaction notes

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