Citric Acid → HCID 44621738, compound

HRID 2427889Notes

Reaction equation

HRID 2427889 reaction equation
CC(C)C[CH:4]([C:8]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[N:11]=[C:10]([N:24]([CH2:35][CH2:36][CH:37]([CH3:39])[CH3:38])[C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)[CH:9]=1)[C:5]([OH:7])=[O:6].C1COCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[OH-].[Na+]>[CH3:38][CH:37]([CH3:39])[CH2:36][CH2:35][N:24]([C:25]1[CH:26]=[CH:27][C:28]([C:31]([F:34])([F:32])[F:33])=[CH:29][CH:30]=1)[C:10]1[CH:9]=[C:8]([CH2:4][C:5]([OH:7])=[O:6])[CH:13]=[C:12]([C:14]2[CH:15]=[CH:16][C:17]([C:20]([F:22])([F:23])[F:21])=[CH:18][CH:19]=2)[N:11]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 8028TetrahydrofuranHCID 45107669HCID 45107669, compound

Product 1

HCID 44621738HCID 44621738, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of [2-[(3-methyl-butyl)-(4-trifluoromethyl-phenyl)-amino]-6-(4-trifluoromethyl-phenyl)-pyridin-4-yl]-acetic acid methyl ester (prepared using 3-methyl-iodo-butane in place of 3-bromo-2-methylprepene as described in Example 41) 55 mg, 0.1 mmol) in NaOH (1N, 0.5 mL) and THF (3 mL) was stirred at 40° C. overnight. The mixture was cooled to room temperature, acidified with 10% citric acid, extracted with CH2Cl2 (3×). The organic layer was washed with brine, dried over Na2SO4, filtered and evaporated. The residue was purified by chromatography (5-20% ethyl acetate in CH2Cl2) to give the product as a white solid (50 mg, 59%). 1H NMR (300 MHz, CDCl3) δ 8.13 (d, J=8.29 Hz, 2H), 7.68 (dd, J=8.48, 13.37 Hz, 4H), 7.38 (d, J=8.29 Hz, 2H), 7.14 (s, 1H), 6.47 (s, 1H), 4.12 (d, J=15.45 Hz, 2H), 3.55 (s, 2H), 1.58-1.68 (m, 3H), 0.96 (d, J=6.40 Hz, 6H). MS m/e 511.2 (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 (5-20% ethyl acetate in CH2Cl2)

Sources & evidence

ORD record
ord-a4dd0c9d9c5c4baa85a360e047d122aa
Source dataset
uspto-grants-2011_06
Patent number
US07968725B2

Reaction notes

Loading…