m-Chloroperbenzoic acid → HCID 11707037, compound

HRID 17078Notes

Reaction equation

HRID 17078 reaction equation
[CH3:1][O:2][C:3](=[O:40])[N:4]([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])[CH2:5][C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[C:8]([S:16][CH3:17])[CH:7]=1.C1C=C(Cl)C=C(C(OO)=[O:49])C=1.OS([O-])=O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:40])[N:4]([CH2:18][C:19]1[CH:24]=[C:23]([C:25]([F:28])([F:26])[F:27])[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])[CH2:5][C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[C:8]([S:16]([CH3:17])=[O:49])[CH:7]=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 (10 mL), 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 (10 mL), 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-aa91a4c60c0c4b6a90380ecf9afdc9fb
Source dataset
uspto-grants-2010_06
Patent number
US07737295B2

Reaction notes

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