Tetrahydrofuran → 4-{[(5-Butanoyl-2-ethylthiophen-3-yl)(cyclohexyl)methyl]amino}benzoic acid

HRID 1877264Notes

Reaction equation

HRID 1877264 reaction equation
[C:1]([C:6]1[S:10][C:9]([CH2:11][CH3:12])=[C:8]([CH:13]([NH:20][C:21]2[CH:30]=[CH:29][C:24]([C:25]([O:27]C)=[O:26])=[CH:23][CH:22]=2)[CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:7]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].O1CCCC1.[OH-].[Na+]>C(O)C>[C:1]([C:6]1[S:10][C:9]([CH2:11][CH3:12])=[C:8]([CH:13]([NH:20][C:21]2[CH:30]=[CH:29][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=2)[CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:7]=1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 68512187Methyl 4-{[(5-butanoyl-2-ethylthiophen-3-yl)(cyclohexyl)methyl]amino}benzoate

Product 1

HCID 685120484-{[(5-Butanoyl-2-ethylthiophen-3-yl)(cyclohexyl)methyl]amino}benzoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of methyl 4-{[(5-butanoyl-2-ethylthiophen-3-yl)(cyclohexyl)methyl]amino}benzoate (316 mg) synthesized above, tetrahydrofuran (5 mL) and ethanol (5 mL) was added 1N aqueous sodium hydroxide solution (5 and the mixture was stirred with heating under reflux for 3 hr, and concentrated under reduced pressure. The residue was dissolved in water (10 mL), and 1N hydrochloric acid (5 mL) was added at 0° C. The resulting precipitate was collected by filtration to give the title compound (290 mg, 95%) as a white solid.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 3 hr
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in water (10 mL)
  5. addition1N hydrochloric acid (5 mL) was added at 0° C
  6. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-c3af9a0f55b342d9a6094893c819fcfa
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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