Lithium Hydroxide → 2-[(4-{2-[(2,4-Difluorobenzyl)(heptyl)amino]-2-oxoethyl}phenoxy)methyl]benzoic acid

HRID 899875Notes

Reaction equation

HRID 899875 reaction equation
[OH-].[Li+].[F:3][C:4]1[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:5]=1[CH2:6][N:7]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:8](=[O:28])[CH2:9][C:10]1[CH:27]=[CH:26][C:13]([O:14][CH2:15][C:16]2[CH:25]=[CH:24][CH:23]=[CH:22][C:17]=2[C:18]([O:20]C)=[O:19])=[CH:12][CH:11]=1>O.C1COCC1>[F:3][C:4]1[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:5]=1[CH2:6][N:7]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:8](=[O:28])[CH2:9][C:10]1[CH:27]=[CH:26][C:13]([O:14][CH2:15][C:16]2[CH:25]=[CH:24][CH:23]=[CH:22][C:17]=2[C:18]([OH:20])=[O:19])=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 69120459Methyl 2-[(4-{2-[(2,4-difluorobenzyl)(heptyl)amino]-2-oxoethyl}phenoxy)methyl]benzoate

Product 1

HCID 100292942-[(4-{2-[(2,4-Difluorobenzyl)(heptyl)amino]-2-oxoethyl}phenoxy)methyl]benzoic acidYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (13.3 mg, 0.554 mmol) in water (1.5 ml) was added into 70335 methyl 2-[(4-{2-[(2,4-difluorobenzyl)(heptyl)amino]-2-oxoethyl}phenoxy)methyl]benzoate (145 mg, 0.277 mmol) dissolved in THF (3 ml). The mixture was then in microwave oven (Smith Synthesizer) at 150° C. for 7 minutes and then evaporated to remove THF. The residue was acidified with 1% hydrochloric acid, pH˜4 and then extracted with ethyl acetate (×2). The organic portions were combined, washed with brine, dried with magnesium sulphate and then evaporated. Chromatography of the residue on a column (ISOLUTE® SI, 2 g/6 ml) using DCM then MeOH/DCM (0.5:99.5, then 1:99) as eluant gave 94 mg desired product, yield 67%.

Workup

  1. customevaporated
  2. customto remove THF
  3. extractionextracted with ethyl acetate (×2)
  4. washwashed with brine
  5. dry with materialdried with magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-a43f7cd115f445c9ab0d011f83b5d4c8
Source dataset
uspto-grants-2008_04
Patent number
US07355069B2

Reaction notes

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