Lithium Hydroxide → 2-[2-(4-{2-[(2,4-Difluorobenzyl)(propyl)amino]-2-oxoethoxy}phenyl)ethoxy]benzoic acid

HRID 898912Notes

Reaction equation

HRID 898912 reaction equation
[F:1][C:2]1[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:3]=1[CH2:4][N:5]([CH2:29][CH2:30][CH3:31])[C:6](=[O:28])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][O:17][C:18]2[CH:27]=[CH:26][CH:25]=[CH:24][C:19]=2[C:20]([O:22]C)=[O:21])=[CH:11][CH:10]=1.[OH-].[Li+]>C1COCC1.O>[F:1][C:2]1[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:3]=1[CH2:4][N:5]([CH2:29][CH2:30][CH3:31])[C:6](=[O:28])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][O:17][C:18]2[CH:27]=[CH:26][CH:25]=[CH:24][C:19]=2[C:20]([OH:22])=[O:21])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 69259573Methyl 2-[2-(4-{2-[(2,4-difluorobenzyl)(propyl)amino]-2-oxoethoxy}phenyl)ethoxy]benzoate

Product 1

HCID 104353942-[2-(4-{2-[(2,4-Difluorobenzyl)(propyl)amino]-2-oxoethoxy}phenyl)ethoxy]benzoic acidYield 84.2%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Methyl 2-[2-(4-{2-[(2,4-difluorobenzyl)(propyl)amino]-2-oxoethoxy}phenyl)-ethoxy]benzoate (0.22 g, 0.442 mmol) was dissolved in a mixture of THF/water (1/1, 4 ml). Lithium hydroxide (0.021 g, 0.884 nmol) was added. The reaction was performed in an single node microwave oven (14 min, 150 deg). Work-up by removing the solvent by evaporation and addition of HCl (2 ml, 1 M). The waterphase was extracted with two portions of EtOAc (20 ml), the organic phase was dried (MgSO4) and the solvent was removed by evaporation to give 0.180 g of 2-[2-(4-{2-[(2,4-difluorobenzyl)(propyl)-amino]-2-oxoethoxy}phenyl)ethoxy]benzoic acid (yield 84.2%).

Workup

  1. customThe reaction was performed in an single node microwave oven
  2. custom(14 min, 150 deg)
  3. customby removing the solvent
  4. customby evaporation and addition of HCl (2 ml, 1 M)
  5. extractionThe waterphase 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

Sources & evidence

ORD record
ord-7e4f408e4ee7488ab399bcaf50fe4bbc
Source dataset
uspto-grants-2008_04
Patent number
US07351858B2

Reaction notes

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