Tetrahydrofuran → 4-{[1-(5-Methoxy-3-methyl-1-benzofuran-2-yl)-5-(methylsulfanyl)pentyl]amino}benzoic acid

HRID 2091235Notes

Reaction equation

HRID 2091235 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH:11]([NH:18][C:19]3[CH:28]=[CH:27][C:22]([C:23]([O:25]C)=[O:24])=[CH:21][CH:20]=3)[CH2:12][CH2:13][CH2:14][CH2:15][S:16][CH3:17])=[C:8]([CH3:29])[C:7]=2[CH:30]=1.O1CCCC1.[OH-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH:11]([NH:18][C:19]3[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:27][CH:28]=3)[CH2:12][CH2:13][CH2:14][CH2:15][S:16][CH3:17])=[C:8]([CH3:29])[C:7]=2[CH:30]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66777286Methyl 4-{[1-(5-methoxy-3-methyl-1-benzofuran-2-yl)-5-(methylsulfanyl)pentyl]amino}benzoate

Product 1

HCID 667778094-{[1-(5-Methoxy-3-methyl-1-benzofuran-2-yl)-5-(methylsulfanyl)pentyl]amino}benzoic acidYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of methyl 4-{[1-(5-methoxy-3-methyl-1-benzofuran-2-yl)-5-(methylsulfanyl)pentyl]amino}benzoate (1.01 g) synthesized above, tetrahydrofuran (10 mL) and ethanol (10 mL) was added 1N aqueous sodium hydroxide solution (10.0 mL), and the mixture was stirred overnight with heating under reflux, and concentrated under reduced pressure. The residue was dissolved in water (20 mL), and 1N hydrochloric acid (10.0 mL) was added at 0° C. The resulting precipitate was collected by filtration to give the title object compound (915 mg, 94%) as a brown solid.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in water (20 mL)
  5. addition1N hydrochloric acid (10.0 mL) was added at 0° C
  6. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-94d37c927fd84991b4458ce5f1674747
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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