Sodium Hydroxide → HCID 17859267, compound

HRID 1372764Notes

Reaction equation

HRID 1372764 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[CH:6]=[C:5]2[C:12]1[O:13][C:14]2[C:20]([F:21])=[C:19]([CH2:22][C:23]([O:25]C)=[O:24])[CH:18]=[CH:17][C:15]=2[N:16]=1.CCCCCC.C(OCC)(=O)C.[OH-].[Na+]>Cl>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[CH:6]=[C:5]2[C:12]1[O:13][C:14]2[C:20]([F:21])=[C:19]([CH2:22][C:23]([OH:25])=[O:24])[CH:18]=[CH:17][C:15]=2[N:16]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226206Ethyl acetate hexaneHCID 58778548HCID 58778548, compound

Product 1

HCID 17859267HCID 17859267, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To methyl (2-(5-fluoro-1-methyl-3-indolyl)-7-fluoro-6-benzoxazolyl)acetate (279 mg, 0.78 mmol) were added THF/methanol (1/1, 20 ml) and 0.25N NaOH (9.4 ml, 2.35 mmol). The resulting mixture was stirred at room temperature for 18 hours. The reaction mixture was poured in 1N HCl to acidify the mixture therewith, followed by extraction with chloroform/methanol (10/1). The extract was dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent. The crystals thus obtained were collected by filtration under reduced pressure, washed with hexane, and dried under reduced pressure to give (2-(5-fluoro-1-methyl-3-indolyl)-7-fluoro-6-benzoxazolyl)acetic acid (208 mg, 78%) as a brown crystalline powder.

Workup

  1. extractionfollowed by extraction with chloroform/methanol (10/1)
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. distillationdistilled under reduced pressure
  4. customto remove the solvent
  5. customThe crystals thus obtained
  6. filtrationwere collected by filtration under reduced pressure
  7. washwashed with hexane
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-6cf6aa2662a743b9b48dd25736319f2e
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

Loading…