Lithium Hydroxide → 2-[(4-{3-[(2,4-Difluorobenzyl)(heptyl)amino]-3-oxopropyl}phenoxy)methyl]benzoic acid

HRID 899878Notes

Reaction equation

HRID 899878 reaction equation
[OH-].[Li+].[F:3][C:4]1[CH:40]=[C:39]([F:41])[CH:38]=[CH:37][C:5]=1[CH2:6][N:7]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:8](=[O:29])[CH2:9][CH2:10][C:11]1[CH:28]=[CH:27][C:14]([O:15][CH2:16][C:17]2[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=2[C:19]([O:21]C)=[O:20])=[CH:13][CH:12]=1>O.C1COCC1>[F:3][C:4]1[CH:40]=[C:39]([F:41])[CH:38]=[CH:37][C:5]=1[CH2:6][N:7]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:8](=[O:29])[CH2:9][CH2:10][C:11]1[CH:28]=[CH:27][C:14]([O:15][CH2:16][C:17]2[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=2[C:19]([OH:21])=[O:20])=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 69120584Methyl 2-[(4-{3-[(2,4-difluorobenzyl)(heptyl)amino]-3-oxopropyl}phenoxy)methyl]benzoate

Product 1

HCID 104144382-[(4-{3-[(2,4-Difluorobenzyl)(heptyl)amino]-3-oxopropyl}phenoxy)methyl]benzoic acidYield 83.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (13.3 mg, 0.554 mmol) in water (1 ml) was added into methyl 2-[(4-{3-[(2,4-difluorobenzyl)(heptyl)amino]-3-oxopropyl}phenoxy)methyl]benzoate (149 mg, 0.277 mmol) dissolved in THF (2 ml). The mixture was then placed 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 extracted with ethyl acetate (×2). The organic extracts were combined and washed with brine and 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 (1:99) as eluant gave 121 mg desired product, yield 83%.

Workup

  1. customThe mixture was then placed in microwave oven
  2. customevaporated
  3. customto remove THF
  4. extractionextracted with ethyl acetate (×2)
  5. washwashed with brine
  6. dry with materialdried with magnesium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-b57d1914dd3c4d7892a2ba099238034b
Source dataset
uspto-grants-2008_04
Patent number
US07355069B2

Reaction notes

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