Sodium Hydroxide → 3-(6-(4,4,4-Trifluoro-1-(4'-(trifluoromethyl)biphenyl-4-yl)butylamino)nicotinamido)propanoic acid

HRID 2407006Notes

Reaction equation

HRID 2407006 reaction equation
[F:1][C:2]([F:39])([F:38])[CH2:3][CH2:4][CH:5]([NH:22][C:23]1[CH:37]=[CH:36][C:26]([C:27]([NH:29][CH2:30][CH2:31][C:32]([O:34]C)=[O:33])=[O:28])=[CH:25][N:24]=1)[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.[OH-].[Na+]>CO>[F:39][C:2]([F:1])([F:38])[CH2:3][CH2:4][CH:5]([NH:22][C:23]1[CH:37]=[CH:36][C:26]([C:27]([NH:29][CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[O:28])=[CH:25][N:24]=1)[C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:13]=[CH:14][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:17]=2)=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86667305Methyl 3-(6-(4,4,4-trifluoro-1-(4'-(trifluoromethyl)biphenyl-4-yl)butylamino)nicotinamido)propanoate

Product 1

HCID 573889383-(6-(4,4,4-Trifluoro-1-(4'-(trifluoromethyl)biphenyl-4-yl)butylamino)nicotinamido)propanoic acidYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-(6-(4,4,4-trifluoro-1-(4′-(trifluoromethyl)biphenyl-4-yl)butylamino) nicotinamido)propanoate (13 mg, 0.023 mmol) was dissolved in 1 mL methanol. 100 μL 1N aqueous sodium hydroxide was added. The resulting solution was stirred at room temperature overnight. The reaction solution was concentrated under reduced pressure. The residue was dissolved in 5 mL water and the solution adjusted to pH 3 by addition of 1N aqueous HCl. The resulting mixture was extracted with ethyl acetate. The organic extract was dried over MgSO4 and concentrated to give a colorless film. Residual solvent was removed under a stream of nitrogen to give 3-(6-(4,4,4-trifluoro-1-(4′-(trifluoromethyl)biphenyl-4-yl)butylamino)nicotinamido)propanoic acid (7.6 mg, 64%) as a colorless solid. 1H NMR (400 MHz, CDCl3) δ 9.24 (br s, 1H), 8.06-8.14 (m, 2H), 7.55-7.65 (m, 4H), 7.52 (d, J=8.2 Hz, 2H), 7.38 (d, J=8.2 Hz, 2H). 6.40 (d, J=9.8 Hz, 1H), 4.46-4.55 (m, 1H), 3.64-3.72 (m, 2H), 2.52-2.59 (m, 2H), 2.04-2.32 (m, 4H). MS (M+H) 540.4.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in 5 mL water
  3. additionthe solution adjusted to pH 3 by addition of 1N aqueous HCl
  4. extractionThe resulting mixture was extracted with ethyl acetate
  5. extractionThe organic extract
  6. dry with materialwas dried over MgSO4
  7. concentrationconcentrated
  8. customto give a colorless film
  9. customResidual solvent was removed under a stream of nitrogen

Sources & evidence

ORD record
ord-dd08337cfbae44b6bfb8ce3fff5422a1
Source dataset
uspto-grants-2014_08
Patent number
US08809342B2

Reaction notes

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