HCID 86614660, compound → HCID 57713313, compound

HRID 1983863Notes

Reaction equation

HRID 1983863 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:29]3[CH:30]=[C:31](OC(=O)C=C)[CH:32]=[CH:33][CH:34]=3)=[C:7]([CH2:13][C:14]([NH:16][C:17]3[C:22]([C:23]([F:26])([F:25])[F:24])=[CH:21][C:20]([F:27])=[CH:19][C:18]=3[OH:28])=[O:15])[C:8](=[O:12])[O:9]2)=[CH:4][C:3]=1[CH3:40]>C1COCC1.C(O)C.[OH-].[Na+]>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:29]3[CH:30]=[C:31](/[CH:6]=[CH:7]/[C:8]([OH:12])=[O:9])[CH:32]=[CH:33][CH:34]=3)=[C:7]([CH2:13][C:14]([NH:16][C:17]3[C:22]([C:23]([F:26])([F:24])[F:25])=[CH:21][C:20]([F:27])=[CH:19][C:18]=3[OH:28])=[O:15])[C:8](=[O:12])[O:9]2)=[CH:4][C:3]=1[CH3:40]

Participants

5

Reactant 1

HCID 86614660HCID 86614660, compound

Product 1

HCID 57713313HCID 57713313, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

Ethyl (2E)-3-{(3-[7-chloro-3-(2-{[4-fluoro-2-hydroxy-6-(trifluoromethyl)phenyl]amino}-2-oxoethyl)-6-methyl-2-oxo-2H-chromen-4-yl]phenyl}acrylate obtained in Reference Example 22 (0.31 g) was dissolved in a mixture of THF (5 ml) and ethanol (5 ml), and 2N aqueous sodium hydroxide solution (1.5 ml) was added thereto. After stirring for 5 hours, the reaction mixture was concentrated. To the residue was added 1N hydrochloric acid and the mixture was extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and concentrated to obtain the title compound as crystals (0.155 g, 52%).

Workup

  1. additionwas added
  2. concentrationthe reaction mixture was concentrated
  3. additionTo the residue was added 1N hydrochloric acid
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e2a69905497a49bb86b7a3085b5dd0f8
Source dataset
uspto-grants-2009_06
Patent number
US07541478B2

Reaction notes

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