Tetrahydrofuran → 4-{[2-Ethyl-1-(3-methyl-1-benzothiophen-2-yl)butyl]amino}benzoic acid

HRID 2091282Notes

Reaction equation

HRID 2091282 reaction equation
[CH2:1]([CH:3]([CH2:26][CH3:27])[CH:4]([NH:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[CH:18][CH:17]=1)[C:5]1[S:6][C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[C:9]=1[CH3:10])[CH3:2].O1CCCC1.[OH-].[Na+]>C(O)C>[CH2:26]([CH:3]([CH2:1][CH3:2])[CH:4]([NH:15][C:16]1[CH:17]=[CH:18][C:19]([C:20]([OH:22])=[O:21])=[CH:24][CH:25]=1)[C:5]1[S:6][C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[C:9]=1[CH3:10])[CH3:27]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66777962Methyl 4-{[2-ethyl-1-(3-methyl-1-benzothiophen-2-yl)butyl]amino}benzoate

Product 1

HCID 667776494-{[2-Ethyl-1-(3-methyl-1-benzothiophen-2-yl)butyl]amino}benzoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of methyl 4-{[2-ethyl-1-(3-methyl-1-benzothiophen-2-yl)butyl]amino}benzoate (580 mg) 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 (529 mg, 95%) as a white 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-fef15a57e4b14fb1a0251f23f02d1ee8
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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