Tetrahydrofuran → HCID 86761834, compound

HRID 2091400Notes

Reaction equation

HRID 2091400 reaction equation
[CH:1]1([CH:6]([NH:18][C:19]2[CH:28]=[CH:27][C:22]([C:23]([O:25]C)=[O:24])=[CH:21][CH:20]=2)[C:7]2[O:8][C:9]3[CH:16]=[CH:15][C:14]([F:17])=[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:18][C:19]2[CH:28]=[CH:27][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=2)[C:7]2[O:8][C:9]3[CH:16]=[CH:15][C:14]([F:17])=[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 Hydroxide2×HCID 86761833HCID 86761833, compound

Product 1

HCID 86761834HCID 86761834, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of methyl 4-{[cyclopentyl(5-fluoro-3-methyl-1-benzofuran-2-yl)methyl]amino}benzoate (1.19 g) synthesized above, tetrahydrofuran (6 mL) and ethanol (6 mL) was added 1N aqueous sodium hydroxide solution (6 mL), and the mixture was stirred with heating under reflux for 3.5 hr. 1N Aqueous sodium hydroxide solution (6 mL) was additionally added to the mixture, and the mixture was stirred with heating under reflux for 14 hr. The reaction mixture was concentrated under reduced pressure, 1N hydrochloric acid (11 mL) was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give the title compound (1.08 g, 94%) as a colorless amorphous form.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 3.5 hr
  3. stirringthe mixture was stirred
  4. temperaturewith heating
  5. temperatureunder reflux for 14 hr
  6. concentrationThe reaction mixture was concentrated under reduced pressure, 1N hydrochloric acid (11 mL)
  7. additionwas added to the residue
  8. extractionthe mixture was extracted with ethyl acetate
  9. washThe extract was washed with saturated brine
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d155e9a16fd341beb2c4458321afa74b
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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