Lithium Hydroxide → HCID 60152348, compound

HRID 537506Notes

Reaction equation

HRID 537506 reaction equation
[CH3:1][CH:2]([CH3:36])[CH2:3][CH:4]([C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[N:29]=[CH:28]2)=[CH:23][CH:22]=1)[O:5][C:6]1[CH:20]=[CH:19][C:9]([C:10]([NH:12][CH2:13][CH2:14][C:15]([O:17]C)=[O:16])=[O:11])=[CH:8][CH:7]=1.[OH-].[Li+]>CO>[CH3:1][CH:2]([CH3:36])[CH2:3][CH:4]([C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH:31]=[C:30]([C:32]([F:34])([F:33])[F:35])[N:29]=[CH:28]2)=[CH:23][CH:22]=1)[O:5][C:6]1[CH:7]=[CH:8][C:9]([C:10]([NH:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[O:11])=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68157773HCID 68157773, compound

Product 1

HCID 60152348HCID 60152348, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-(4-(3-methyl-1-(4-(4-(trifluoromethyl)-1H-imidazol-1-yl)phenyl)butoxy)benzamido)propanoate (70 mg, 0.14 mmol) was dissolved in methanol (2 mL) and 1M lithium hydroxide (1 mL) was added. The reaction was stirred at room temperature for 1 hour. The methanol was removed under reduced pressure and the residue was diluted with water (2 mL). Upon stirring a precipitate forms. The solution was further diluted with water (15 mL) and 1M NaOH (3 mL). The solution was extracted with ether (20 mL). The organics were washed with water (10 mL) and the aqueous layers were combined. The aqueous solution was acidified with 1M HCl to give a cloudy solution. The solution was extracted with ethyl acetate (2×15 mL). The combined organics were dried over sodium sulfate, filtered and concentrated to give (+/−)-3-(4-(3-methyl-1-(4-(4-(trifluoromethyl)-1H-imidazol-1-yl)phenyl)butoxy)benzamido)propanoic acid (53.1 mg, 78%) as an off-white solid. 1H NMR (400 MHz, CDCl3, δ): 7.89 (s, 1H), 7.66-7.60 (m, 2H), 7.58 (s, 1H), 7.49 (d, J=8.5 Hz, 2H), 7.36 (d, J=8.5 Hz, 2H), 6.97-6.92 (m, 2H), 6.77 (t, J=6 Hz, 1H), 5.29 (dd, J=9, 4.4 Hz, 1H), 3.73-3.63 (m, 2H), 2.66-2.64 (m, 2H), 2.06-2.00 (m, 1H), 1.95-1.83 (m, 1H), 1.62 (m, 1H), 1.03 (d, J=6.6 Hz, 3H), 0.99 (d, J=6.6 Hz, 3H). MS (M+1): 490.2.

Workup

  1. customThe methanol was removed under reduced pressure
  2. additionthe residue was diluted with water (2 mL)
  3. stirringUpon stirring a precipitate forms
  4. additionThe solution was further diluted with water (15 mL) and 1M NaOH (3 mL)
  5. extractionThe solution was extracted with ether (20 mL)
  6. washThe organics were washed with water (10 mL)
  7. customto give a cloudy solution
  8. extractionThe solution was extracted with ethyl acetate (2×15 mL)
  9. dry with materialThe combined organics were dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-673f457819ca4e37ac8b044543e38c16
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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