Methanol → 3-(4-(1-(2-methyl-4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenoxy)butyl)benzamido)-propanoic acid

HRID 537565Notes

Reaction equation

HRID 537565 reaction equation
[CH3:1][C:2]1[CH:28]=[C:27]([N:29]2[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[N:30]2)[CH:26]=[CH:25][C:3]=1[O:4][CH:5]([C:9]1[CH:24]=[CH:23][C:12]([C:13]([NH:15][CH2:16][CH2:17][C:18]([O:20]CC)=[O:19])=[O:14])=[CH:11][CH:10]=1)[CH2:6][CH2:7][CH3:8].O.[OH-].[Li+].CO.C1COCC1>O>[CH3:1][C:2]1[CH:28]=[C:27]([N:29]2[CH:33]=[C:32]([C:34]([F:35])([F:37])[F:36])[CH:31]=[N:30]2)[CH:26]=[CH:25][C:3]=1[O:4][CH:5]([C:9]1[CH:24]=[CH:23][C:12]([C:13]([NH:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[O:14])=[CH:11][CH:10]=1)[CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 68156556ethyl 3-(4-(1-(2-methyl-4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenoxy)butyl)benzamido)propanoate

Product 1

HCID 681567003-(4-(1-(2-methyl-4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenoxy)butyl)benzamido)-propanoic acidYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 3-(4-(1-(2-methyl-4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenoxy)butyl)-benzamido)propanoate (55 mg, 0.11 mmol), lithium hydroxide monohydrate (7.2 mg, 0.3 mmol), methanol (2 ml), THF (2 ml), and water (0.3 ml) was stirred at 220 for 3 days. The mixture was concentrated, diluted with 8 ml of water and 0.35 ml of 1 M potassium hydrogen sulfate. The mixture was extracted with ethyl acetate, the extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated to obtain 3-(4-(1-(2-methyl-4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenoxy)butyl)benzamido)-propanoic acid as a white solid (50 mg, 96%). 1H NMR (500 MHz, CDCl3) δ 8.00 (s, 1H), 7.84 (s, 1H), 7.73 (d, J=8.29 Hz, 2H), 7.43 (d, J=2.68 Hz, 1H), 7.39 (d, J=8.29 Hz, 2H), 7.18 (dd, J=2.68, 8.78 Hz, 1H), 6.84-6.90 (m, 1H), 6.59 (d, J=8.78 Hz, 1H), 5.20 (dd, J=5.12, 7.56 Hz, 1H), 3.71 (q, J=5.94 Hz, 2H), 2.69 (t, J=5.85 Hz, 2H), 2.39 (s, 3H), 1.99-2.09 (m, 1H), 1.80-1.89 (m, 1H), 1.51-1.61 (m, 1H), 1.42-1.50 (m, 1H), 0.98 (t, J=7.32 Hz, 3H). MS (M+1): 4902.

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with 8 ml of water and 0.35 ml of 1 M potassium hydrogen sulfate
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5d4109bfd4b942e088641132c392da5f
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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