Hydrochloric Acid → 5-[Imino[[(phenylmethoxy)carbonyl]amino]methyl]furo[2,3-b]pyridine-2-carboxylic acid

HRID 1682690Notes

Reaction equation

HRID 1682690 reaction equation
Cl.[C:2]([C:5]1[CH:6]=[C:7]2[CH:13]=[C:12]([C:14]([O:16]CC)=[O:15])[O:11][C:8]2=[N:9][CH:10]=1)(=[NH:4])[NH2:3].Cl[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21].[OH-].[Na+].Cl>O1CCCC1>[CH2:23]([O:22][C:20]([NH:3][C:2]([C:5]1[CH:6]=[C:7]2[CH:13]=[C:12]([C:14]([OH:16])=[O:15])[O:11][C:8]2=[N:9][CH:10]=1)=[NH:4])=[O:21])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2×HCID 18919443HCID 18919443, compound

Product 1

HCID 1403812475-[Imino[[(phenylmethoxy)carbonyl]amino]methyl]furo[2,3-b]pyridine-2-carboxylic acidYield 40.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Tetrahydrofuran (32 ml) was added to ethyl 5-amidinofuro[2,3-b]pyridine-2-carboxylate hydrochloride (2.05 g, 5.10 mmol), and benzyl chloroformate (1.09 ml, 7.65 mmol) was dropwise added under ice-cooling while maintaining the mixture at pH 10-12 with a 1N aqueous sodium hydroxide solution. Thereafter, the mixture was stirred under ice-cooling for 30 minutes and at room temperature for 1.5 hours. Tetrahydrofuran (20 ml) and a 1N aqueous sodium hydroxide solution (20 ml) were added to this reaction mixture and the mixture was stirred at room temperature for 1.5 hours. The mixture was adjusted to pH 4-5 with 1N hydrochloric acid and low boiling matters were distilled away under reduced pressure. The residue was purified by reversed-phase column (Chromatorex-ODS DM1020T, Fuji Silysia Chemical) chromatography. (water-acetonitrile) to give 695 mg of 5-(benzyloxycarbonylamidino)furo[2,3-b]pyridine-2-carboxylic acid as a yellow solid (35%).

Workup

  1. additionwas dropwise added under ice-
  2. temperaturecooling
  3. stirringthe mixture was stirred at room temperature for 1.5 hours
  4. distillationwere distilled away under reduced pressure
  5. customThe residue was purified by reversed-phase column (Chromatorex-ODS DM1020T, Fuji Silysia Chemical) chromatography

Sources & evidence

ORD record
ord-cb2bc30ce4ef4c8990f7fd4ca9b56920
Source dataset
uspto-grants-1997_06
Patent number
US05635527

Reaction notes

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