Water → (4-{[(6-Chloro-3-{[(3-chlorophenyl)methyl]oxy}-2-fluorophenyl)carbonyl]amino}phenyl)acetic acid

HRID 1879123Notes

Reaction equation

HRID 1879123 reaction equation
[OH-].[Li+].[Cl:3][C:4]1[C:9]([C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22]CC)=[O:21])=[CH:15][CH:14]=2)=[O:11])=[C:8]([F:25])[C:7]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=2)=[CH:6][CH:5]=1.O>O1CCOCC1>[Cl:3][C:4]1[C:9]([C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]([OH:22])=[O:21])=[CH:15][CH:14]=2)=[O:11])=[C:8]([F:25])[C:7]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 59163349Ethyl (4-{[(6-chloro-3-{[(3-chlorophenyl)methyl]oxy}-2-fluorophenyl)carbonyl]amino}phenyl)acetate

Product 1

HCID 24957187(4-{[(6-Chloro-3-{[(3-chlorophenyl)methyl]oxy}-2-fluorophenyl)carbonyl]amino}phenyl)acetic acidYield 32%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Lithium hydroxide monohydate (12 mg, 0.281 mmol) was added to a solution of ethyl (4-{[(6-chloro-3-{[(3-chlorophenyl)methyl]oxy}-2-fluorophenyl)carbonyl]amino}phenyl)acetate (91 mg, 0.192 mmol in dioxane (2 ml) and water (1 ml) and the reaction was stirred at room temperature overnight. The solvent was evaporated, the residue dissolved in water (5 ml) and acidified (2M HCl, pH˜1). The aqueous layer was extracted with ethyl acetate, the organics dried (Na2SO4) and the solvent evaporated to afford a colourless solid which was collected by filtration. This was purified by mass directed auto-prep (MDAP) to afford the title compound as a colourless solid (28 mg, 32%).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in water (5 ml)
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialthe organics dried (Na2SO4)
  5. customthe solvent evaporated
  6. customto afford a colourless solid which
  7. filtrationwas collected by filtration
  8. customThis was purified by mass

Sources & evidence

ORD record
ord-0b539bbeb7c844769870bd215afea26f
Source dataset
uspto-grants-2012_11
Patent number
US08314147B2

Reaction notes

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