Lithium Hydroxide → 2-[(3-{2-[Benzyl(hexyl)amino]-2-oxoethyl}phenoxy)methyl]benzoic acid

HRID 2111974Notes

Reaction equation

HRID 2111974 reaction equation
[CH2:1]([N:8]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:9](=[O:29])[CH2:10][C:11]1[CH:12]=[C:13]([CH:26]=[CH:27][CH:28]=1)[O:14][CH2:15][C:16]1[CH:25]=[CH:24][CH:23]=[CH:22][C:17]=1[C:18]([O:20]C)=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+]>C1COCC1.O>[CH2:1]([N:8]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:9](=[O:29])[CH2:10][C:11]1[CH:12]=[C:13]([CH:26]=[CH:27][CH:28]=1)[O:14][CH2:15][C:16]1[CH:25]=[CH:24][CH:23]=[CH:22][C:17]=1[C:18]([OH:20])=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68873954HCID 68873954, compound

Product 1

HCID 104569222-[(3-{2-[Benzyl(hexyl)amino]-2-oxoethyl}phenoxy)methyl]benzoic acidYield 12.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-[(3-{2-[benzyl(hexyl)amino]-2-oxoethyl}phenoxy)methyl]benzoate (59 mg, 0.125 mmol) in THF (1 ml) was cooled in an ice-bath. Lithium hydroxide (6 mg, 0.249 mmol) in water (1 ml) was dropped in. The cooling-bath was then removed and the mixture was stirred for 13 days and then evaporated in vacuum to remove THF. The residue was acidified with 1% hydrochloric acid, pH˜4, and extracted with ethyl acetate. The organic phase was dried (magnesium sulphate) and evaporated. Chromatography of the residue on a column (ISOLUTE® SI, 1 g/6 ml) using DCM and MeOH/DCM (0.5:99.5, then 1:99) as eluant gave 7 mg the desired product, yield 8% (two steps).

Workup

  1. customThe cooling-bath was then removed
  2. customevaporated in vacuum
  3. customto remove THF
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase was dried (magnesium sulphate)
  6. customevaporated

Sources & evidence

ORD record
ord-4c3d44174d9f429fb628cca172feed77
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Reaction notes

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