Hydrochloric Acid → (4-{2-[Benzyl(hexyl)amino]-2-oxoethyl}-2-fluorophenoxy methyl]benzoic acid

HRID 2111990

Reaction equation

HRID 2111990 reaction equation
[CH2:1]([N:8]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:9](=[O:30])[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])=[C:13]([F:29])[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+].Cl>C1COCC1.O>[CH2:1]([N:8]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:9](=[O:30])[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])=[C:13]([F:29])[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68869229Methyl 2-[(4-{2-[benzyl(hexyl)amino]-2-oxoethyl}-2-fluorophenoxy)methyl]benzoate

Product 1

HCID 10322789(4-{2-[Benzyl(hexyl)amino]-2-oxoethyl}-2-fluorophenoxy methyl]benzoic acidYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-[(4-{2-[benzyl(hexyl)amino]-2-oxoethyl}-2-fluorophenoxy)methyl]benzoate (109 mg, 0.222 mmol) was dissolved in THF (2 ml). Lithium hydroxide (10.6 mg, 0.444 mmol) solved in water (1 ml) was added. The mixture was put in a microwave oven (Smith Synthesizer) at 150° C. for 7 minutes. It was then acidified with 1% hydrochloric acid, pH˜3, and extracted with ethyl acetate. The organic extract was washed with brine and dried (magnesium sulphate) and evaporated. Chromatography of the residue on a column (ISOLUTE® SI, 2 g/6 ml) using DCM and then MeOH/DCM (0.5: 99.5, then 1:99) as eluant gave 89 mg the desired product, yield 84%.

Workup

  1. additionwas added
  2. customThe mixture was put in a microwave oven
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried (magnesium sulphate)
  7. customevaporated

Sources & evidence

ORD record
ord-e80d9b33920e4055bb9f01779985d5e6
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Linked notes

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