Potassium Hydroxide → 2-[(4-{2-[Ethyl(2-fluorobenzyl)amino]-2-oxoethoxy}phenoxy)methyl]benzoic acid

HRID 2112054Notes

Reaction equation

HRID 2112054 reaction equation
[CH2:1]([N:3]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[F:33])[C:4](=[O:25])[CH2:5][O:6][C:7]1[CH:24]=[CH:23][C:10]([O:11][CH2:12][C:13]2[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=2[C:15]([O:17]C)=[O:16])=[CH:9][CH:8]=1)[CH3:2].[OH-].[K+]>CCO>[CH2:1]([N:3]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[F:33])[C:4](=[O:25])[CH2:5][O:6][C:7]1[CH:24]=[CH:23][C:10]([O:11][CH2:12][C:13]2[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=2[C:15]([OH:17])=[O:16])=[CH:9][CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 68869777Methyl 2-[(4-{2-[ethyl(2-fluorobenzyl)amino]-2-oxoethoxy}phenoxy)methyl]benzoate

Product 1

HCID 100487092-[(4-{2-[Ethyl(2-fluorobenzyl)amino]-2-oxoethoxy}phenoxy)methyl]benzoic acidYield 68.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 2-[(4-{2-[ethyl(2-fluorobenzyl)amino]-2-oxoethoxy}phenoxy)methyl]-benzoate (0.242 g, 0.536 mmol) was dissolved in EtOH (5 ml, 95%), potassium hydroxide (0.060 g, 1.072 mmol) was added. The reaction was performed in an single node microwave oven (7 min, 150° C.). Work-up was by removing the solvent by evaporation and addition of HCl (2 ml, 1 M). The water-phase was extracted with two portions of EtOAc (20 ml) and the organic phase was dried (MgSO4) and the solvent was removed by evaporation. The crude was purified by flash chromatography (started with isocratic DCM 100% and then the MeOH concentration was increased from 0.5% to 20%, (silica gel 60 0.004-0.063 mm). The product containing fractions were pooled and the EtOAc was removed by evaporation to give 0.160 g of 2-[(4-{2-[ethyl(2-fluorobenzyl)amino]-2-oxoethoxy}phenoxy)methyl]benzoic acid (yield 68.2%).

Workup

  1. customThe reaction was performed in an single node microwave oven
  2. custom(7 min, 150° C.)
  3. customby removing the solvent
  4. customby evaporation and addition of HCl (2 ml, 1 M)
  5. extractionThe water-phase was extracted with two portions of EtOAc (20 ml)
  6. dry with materialthe organic phase was dried (MgSO4)
  7. customthe solvent was removed by evaporation
  8. customThe crude was purified by flash chromatography (
  9. concentrationthe MeOH concentration
  10. temperaturewas increased from 0.5% to 20%, (silica gel 60 0.004-0.063 mm)
  11. additionThe product containing fractions
  12. customthe EtOAc was removed by evaporation

Sources & evidence

ORD record
ord-3ff98633bbe74004ae42d7b90d0d297d
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Reaction notes

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