Hydrochloric Acid → HCID 19611729, compound

HRID 1602576Notes

Reaction equation

HRID 1602576 reaction equation
CO[C:3]([CH2:5][NH:6][CH:7]([CH3:33])[CH:8]([C:24]1[CH:29]=[CH:28][C:27]2[O:30][CH2:31][O:32][C:26]=2[CH:25]=1)[CH2:9][C:10]1[O:11][C:12]([C:15](=[O:23])[NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:13][CH:14]=1)=[O:4].[OH-].[Na+].Cl>O1CCCC1>[C:17]1([NH:16][C:3]([CH2:5][NH:6][CH:7]([CH3:33])[CH:8]([C:24]2[CH:25]=[CH:26][C:27]3[O:30][CH2:31][O:32][C:28]=3[CH:29]=2)[CH2:9][C:10]2[O:11][C:12]([C:15](=[O:23])[NH:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:13][CH:14]=2)=[O:4])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19611720HCID 19611720, compound

Product 1

HCID 19611729HCID 19611729, compoundYield 113%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

159 mg of N-(methoxycarbonylmethyl)-[(1RS,2RS)-1-methyl-2-(3,4-methylenedioxyphenyl)-3-{5-(phenylcarbamoyl)-2-furyl}propyl]amine in 5 ml of tetrahydrofuran was stirred together with 0.3 ml of 4N aqueous sodium hydroxide at room temperature for 1.5 hours. The reaction solution was acidified with 1N hydrochloric acid and then extracted with ethyl acetate, and the extract was dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the solvent was distilled off under reduced pressure. The residue was dissolved in 3 ml of dimethylformamide and stirred together with 161 mg of aniline and 98 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride at room temperature for 17 hours. After addition of water, the reaction solution was extracted with ethyl acetate, and the extract was washed with 1N aqueous sodium hydroxide and saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel thin layer chromatography [Kieselgel™60F254, Art™5717; hexane/ethyl acetate=1/1] to give 102 mg of the title compound as a colorless foamy substance.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialthe extract was dried over anhydrous magnesium sulfate
  3. filtrationThe desiccant was filtered off
  4. distillationthe solvent was distilled off under reduced pressure
  5. dissolutionThe residue was dissolved in 3 ml of dimethylformamide
  6. additionAfter addition of water
  7. extractionthe reaction solution was extracted with ethyl acetate
  8. washthe extract was washed with 1N aqueous sodium hydroxide and saturated aqueous sodium chloride
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationThe desiccant was filtered off
  11. distillationthe solvent was distilled off under reduced pressure
  12. customThe residue was purified by silica gel thin layer chromatography [Kieselgel™60F254, Art™5717; hexane/ethyl acetate=1/1]

Sources & evidence

ORD record
ord-671240bddcee45bbb88546f3c6834e9a
Source dataset
uspto-grants-1999_11
Patent number
US05981573

Reaction notes

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