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

HRID 2091079Notes

Reaction equation

HRID 2091079 reaction equation
[CH:1]1([CH:6]([NH:17][C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24]C)=[O:23])=[CH:20][CH:19]=2)[C:7]2[S:8][C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[C:11]=2[CH3:12])[CH2:5][CH2:4][CH2:3][CH2:2]1.O1CCCC1.[OH-].[Na+]>C(O)C>[CH:1]1([CH:6]([NH:17][C:18]2[CH:27]=[CH:26][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=2)[C:7]2[S:8][C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[C:11]=2[CH3:12])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66778514Methyl 4-{[cyclopentyl(3-methyl-1-benzothiophen-2-yl)methyl]amino}benzoate

Product 1

HCID 667776404-{[Cyclopentyl(3-methyl-1-benzothiophen-2-yl)methyl]amino}benzoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of methyl 4-{[cyclopentyl(3-methyl-1-benzothiophen-2-yl)methyl]amino}benzoate (1.56 g) synthesized above, tetrahydrofuran (20 mL) and ethanol (20 mL) was added 1N aqueous sodium hydroxide solution (20.0 mL), and the mixture was stirred with heating under reflux for 4 hr, and concentrated under reduced pressure. The residue was dissolved in water (40 mL), and 1N hydrochloric acid (20.0 mL) was added at 0° C. The resulting precipitate was collected by filtration, and the obtained pale-brown solid was dissolved in ethyl acetate. The solution was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give the title object compound (1.42 g, 95%) as a pale-brown solid.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 4 hr
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in water (40 mL)
  5. addition1N hydrochloric acid (20.0 mL) was added at 0° C
  6. filtrationThe resulting precipitate was collected by filtration
  7. dissolutionthe obtained pale-brown solid was dissolved in ethyl acetate
  8. washThe solution was washed with saturated brine
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3d725fd01a0e4b089e9a4adc9cc7bd4a
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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