Dicyclohexylcarbodiimide → 3-Fluoro-4-(2-methyloctanoyl) phenyl-3-fluoro-4-heptyloxy benzoic acid

HRID 2372258Notes

Reaction equation

HRID 2372258 reaction equation
[F:1][C:2]1[CH:3]=[C:4](O)[CH:5]=[CH:6][C:7]=1[C:8](=[O:17])[CH:9]([CH3:16])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[F:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][C:28]=1[O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:23]([OH:25])=[O:24].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([C:21]2[C:20]([F:19])=[C:28]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH:27]=[CH:26][C:22]=2[C:23]([OH:25])=[O:24])[CH:5]=[CH:6][C:7]=1[C:8](=[O:17])[CH:9]([CH3:16])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 15027241(+)-3-Fluoro 4-(2-methyloctanoyl) phenolHCID 150272423-Fluoro-4-heptyloxy benzoic acid

Product 1

HCID 678527963-Fluoro-4-(2-methyloctanoyl) phenyl-3-fluoro-4-heptyloxy benzoic acidYield 56.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a flask were charged 1.2 g (4.76 mmol) of (+)-3-fluoro 4-(2-methyloctanoyl) phenol, 1.51 g (5.94 mmol) of 3-fluoro-4-heptyloxy benzoic acid, 76.7 mg (0.63 mmol) of N,N-dimethylamino pyridine and 30 ml of dried methylene chloride, which were slightly heated with stirring to form a homogeneous solution. Then, the solution was added with 1.40 g (6.79 mmol) of dicyclohexyl carbodiimide and stirred over a night. The precipitated white crystal was filtered off, and the resulting filtrate was washed with 2 normal hydrochloric acid, an aqueous solution of 5% sodium hydrogen carbonate and water in this order and dried on magnesium sulfate. After magnesium sulfate was filtered off, the filtrate was concentrated and dried under a reduced pressure to obtain an oil. This oil was purified through a column chromatography and recrystallized with ethanol to obtain 1.02 g (2.69 mmol, yield: 44%) of a white crystal of the objective compound having the aforementioned physical and chemical properties.

Workup

  1. temperaturewere slightly heated
  2. customto form a homogeneous solution
  3. stirringstirred over a night
  4. filtrationThe precipitated white crystal was filtered off
  5. washthe resulting filtrate was washed with 2 normal hydrochloric acid
  6. dry with materialan aqueous solution of 5% sodium hydrogen carbonate and water in this order and dried on magnesium sulfate
  7. filtrationAfter magnesium sulfate was filtered off
  8. concentrationthe filtrate was concentrated
  9. customdried under a reduced pressure
  10. customto obtain an oil
  11. customThis oil was purified through a column chromatography
  12. customrecrystallized with ethanol

Sources & evidence

ORD record
ord-df0c5c526fe04e92afc9ffd23c9ed1ec
Source dataset
uspto-grants-1992_03
Patent number
US05098602

Reaction notes

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