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 2288507Notes

Reaction equation

HRID 2288507 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.butoxycarbonyl-amino)acetylamino]-4-methylamino-benzoic 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 sulphate. 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 the combined organic phases
  6. washwere washed with saline solution
  7. dry with materialdried over sodium sulphate
  8. customAfter evaporation of the solvent the crude product
  9. customwas chromatographed on silica gel
  10. washeluting first with methylene chloride
  11. customevaporated down

Sources & evidence

ORD record
ord-53ea0cf109ed4c69831199c9d1ac6191
Source dataset
uspto-grants-2000_07
Patent number
US06087380

Reaction notes

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