Citric Acid → HCID 45108074, compound

HRID 2427869Notes

Reaction equation

HRID 2427869 reaction equation
C[O:2][C:3](=[O:35])[CH:4]([C:9]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)[N:12]=[C:11]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)[CH:10]=1)[CH2:5][CH:6]([CH3:8])[CH3:7].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[OH-].[Na+].C1COCC1>[F:34][C:31]([F:32])([F:33])[C:28]1[CH:29]=[CH:30][C:25]([C:11]2[CH:10]=[C:9]([CH:4]([CH2:5][CH:6]([CH3:8])[CH3:7])[C:3]([OH:35])=[O:2])[CH:14]=[C:13]([C:15]3[CH:16]=[CH:17][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:20]=3)[N:12]=2)=[CH:26][CH:27]=1

Participants

5

Reactant 2

HCID 311Citric AcidHCID 59161732HCID 59161732, compound

Product 1

HCID 45108074HCID 45108074, compoundYield 78.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 2-[2,6-bis-(4-trifluoromethyl-phenyl)-pyridin-4-yl]-4-methyl-pentanoic acid methyl ester (250 mg, 0.5 mmol) in NaOH (1N, 1 mL) and THF (5 mL) was stirred at 40° C. overnight. The mixture was cooled to room temperature, acidified with 10% citric acid, and extracted with CH2Cl2 (3×). The organic layer was washed with brine, dried over Na2SO4, filtered and evaporated. The residue was purified by chromatography (5-25% ethyl acetate in CH2Cl2) to give the product as a white solid (190 mg, 78%). 1H NMR (300 MHz, CDCl3) δ 8.23 (d, J=8.29 Hz, 4H), 7.68-7.83 (m, 6H), 3.85 (t, J=7.72 Hz, 1H), 2.05-2.17 (m, 1H), 1.79 (dt, J=7.06, 13.75 Hz, 1H), 1.53-1.64 (m, 1H), 0.98 (d, J=6.40 Hz, 6H). MS m/e 482.2 (M+H).

Workup

  1. extractionextracted with CH2Cl2 (3×)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography (5-25% ethyl acetate in CH2Cl2)

Sources & evidence

ORD record
ord-a3b953c24bdc415abb49eabbe80419ea
Source dataset
uspto-grants-2011_06
Patent number
US07968725B2

Reaction notes

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