Ethyl Acetate → HCID 58968712, compound

HRID 2075105Notes

Reaction equation

HRID 2075105 reaction equation
[F:1][C:2]([F:41])([F:40])[C:3]1[CH:4]=[C:5]([CH:33]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:35]=1)[CH2:6][N:7]([CH2:14][C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:16]=1[C:25](=[O:32])[CH2:26][CH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1)[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1.[CH3:42][Mg]Br.C(OCC)(=O)C>C1COCC1>[F:39][C:36]([F:37])([F:38])[C:34]1[CH:33]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:40])[F:41])[CH:35]=1)[CH2:6][N:7]([CH2:14][C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:16]=1[C:25]([OH:32])([CH3:42])[CH2:26][CH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1)[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 58968639HCID 58968639, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 58968712HCID 58968712, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,-(2-(((3,5-bis(trifluoromethyl)benzyl)(2-methyl-2-H-tetrazol-5-yl)amino)methyl)-4-(trifluoromethyl)phenyl-2-cyclopentylethanone (160 mg, 0.269 mmol) in anhydrous THF (10 mL) at 0° C. was added methylmagnesium bromide (3.0 M solution in THF, 0.359 mL, 1.07 mmol). After stirring for 30 minutes the solution was warmed to room temp and stirred for 1.5 hours. After 1.5 hours solution was portioned between 2 N HCL (10 mL) and ethyl acetate (20 mL). The mixture was stirred at room temperature for 10 minutes before the layers were separated. The aqueous layer was extracted with ethyl acetate (3×15 mL). The combined organics layers were dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give a yellow oil. (160 mg, 97%). 1H NMR (400 MHz, CDCl3) δ 7.72 (s, 1H) 7.67(s, 2H) 7.38 (m, 3H) 5.32 (d, J=16.6 Hz, 1H) 5.01 (d, J=16.6 Hz, 1H) 4.78 (s, 2H) 4.13 (s, 3H) 1.92 (dd, J=5.4 Hz, J=5.4 Hz) 1.80 (dd, J=5.81 Hz, J=6.24 Hz) 1.64 (m, 2H) 1.59 (s, 3H) 1.54 (m, 3H) 1.35 (m, 2H) 0.88 (m, 2H). LC-MS Calc. 609.5, found 610.5 (M+H).

Workup

  1. stirringstirred for 1.5 hours
  2. stirringThe mixture was stirred at room temperature for 10 minutes before the layers
  3. customwere separated
  4. extractionThe aqueous layer was extracted with ethyl acetate (3×15 mL)
  5. dry with materialThe combined organics layers were dried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a yellow oil

Sources & evidence

ORD record
ord-ff4d04bf531c4807926161ffc27b10c1
Source dataset
uspto-grants-2011_04
Patent number
US07919506B2

Reaction notes

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