3-[(N-tert-butoxycarbonylamino)acetylaminoj-4-methylaminobenzoic acid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide → 1-Methyl-2-(n-tert-butoxycarbonylaminomethyl)benzimidazol-5-yl-carboxylic acid-n-(2-pyridyl)-n-(2-ethoxycarbonylethyl)amide

HRID 50370Notes

Reaction equation

HRID 50370 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]([CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:8](=[O:29])[C:9]1[CH:14]=[CH:13][C:12]([NH:15][CH3:16])=[C:11]([NH:17][C:18](=O)[CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:10]=1>C(O)(=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]([CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:8]([C:9]1[CH:14]=[CH:13][C:12]2[N:15]([CH3:16])[C:18]([CH2:19][NH:20][C:21]([O:23][C:24]([CH3:26])([CH3:27])[CH3:25])=[O:22])=[N:17][C:11]=2[CH:10]=1)=[O:29]

Participants

3

Reactant 1

HCID 698927693-[(N-tert-butoxycarbonylamino)acetylaminoj-4-methylaminobenzoic acid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide

Product 1

HCID 184126741-Methyl-2-(n-tert-butoxycarbonylaminomethyl)benzimidazol-5-yl-carboxylic acid-n-(2-pyridyl)-n-(2-ethoxycarbonylethyl)amide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

10.0 g (0.02 mol) of 3-[(N-tert-butoxycarbonylamino)acetylamino]-4-methylaminobenzoic acid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)amide were dissolved in 50 mL of glacial acetic acid and refluxed for one hour. Then the solvent was distilled off, the residue was mixed with ice water and adjusted to pH 8 by the addition of 2N ammonia. After extraction three times with ethyl acetate, the combined organic phases were washed with saline solution and dried over sodium sulfate. After evaporation of the solvent, the crude product was chromatographed on silica gel, eluting first with methylene chloride, then with methylene chloride/ethanol (50:1) and (25:1). The desired fractions were combined and evaporated down. Yield: 5.85 g (61% of theory), C25H31N5O5 (481.6); Rf value: 0.70 (silica gel; methylene chloride/ethanol=9:1).

Workup

  1. temperaturerefluxed for one hour
  2. distillationThen the solvent was distilled off
  3. additionthe residue was mixed with ice water
  4. additionadjusted to pH 8 by the addition of 2N ammonia
  5. extractionAfter extraction three times with ethyl acetate
  6. washthe combined organic phases were washed with saline solution
  7. dry with materialdried over sodium sulfate
  8. customAfter evaporation of the solvent
  9. customthe crude product was chromatographed on silica gel
  10. washeluting first with methylene chloride
  11. customevaporated down

Sources & evidence

ORD record
ord-935edc60dd36453f97fb77b7b246854f
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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