Potassium Hydroxide → 2-[(4-{2-[Ethyl(2-fluorobenzyl)amino]-2-oxoethyl}benzyl)oxy]benzoic acid

HRID 2112056Notes

Reaction equation

HRID 2112056 reaction equation
[CH2:1]([N:3]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[F:32])[C:4](=[O:24])[CH2:5][C:6]1[CH:23]=[CH:22][C:9]([CH2:10][O:11][C:12]2[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=2[C:14]([O:16]C)=[O:15])=[CH:8][CH:7]=1)[CH3:2].[OH-].[K+]>CCO>[CH2:1]([N:3]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[F:32])[C:4](=[O:24])[CH2:5][C:6]1[CH:23]=[CH:22][C:9]([CH2:10][O:11][C:12]2[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=2[C:14]([OH:16])=[O:15])=[CH:8][CH:7]=1)[CH3:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 68870269Methyl 2-[(4-(2-[ethyl(2-fluorobenzyl)amino]-2-oxoethyl)benzyl)oxy]benzoate

Product 1

HCID 100478062-[(4-{2-[Ethyl(2-fluorobenzyl)amino]-2-oxoethyl}benzyl)oxy]benzoic acidYield 5.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 2-[(4-{2-[ethyl(2-fluorobenzyl)amino]-2-oxoethyl}benzyl)oxy]benzoate (0.242 g, 0.555 mmol) was dissolved in EtOH (5 ml, 95%), potassium hydroxide (0.062 g, 1.111 mmol) was added. The reaction was performed in an single node microwave oven (7 min, 150° C.). Work-up 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 0.013 g of 2-[(4-{2-[ethyl(2-fluorobenzyl)amino]-2-oxoethyl}benzyl)oxy]benzoic acid (yield 5.6%).

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-95a866ff688244619f2659101e636a00
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Reaction notes

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