Ethyl 3-{5-[(4-nitrobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate → 3-{5-[(4-Nitrobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoic acid

HRID 1676042Notes

Reaction equation

HRID 1676042 reaction equation
[N+:1]([C:4]1[CH:34]=[CH:33][C:7]([C:8]([NH:10][C:11]2[CH:32]=[CH:31][C:14]3[N:15]([CH:18]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH2:19][C:20]([O:22]CC)=[O:21])[CH:16]=[N:17][C:13]=3[CH:12]=2)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]>C(#N)C.Cl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:10][C:11]2[CH:32]=[CH:31][C:14]3[N:15]([CH:18]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH2:19][C:20]([OH:22])=[O:21])[CH:16]=[N:17][C:13]=3[CH:12]=2)=[O:9])=[CH:33][CH:34]=1)([O-:3])=[O:2]

Participants

4

Reactant 1

HCID 58653626Ethyl 3-{5-[(4-nitrobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate

Product 1

HCID 586536733-{5-[(4-Nitrobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of ethyl 3-{5-[(4-nitrobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate (60 mg, 131 μmol) in a mixture of acetonitrile (10 mL) and hydrochloric acid (20 mL of a 5N solution) was stirred at room temperature for 72 hours. The resulting precipitate was collected by filtration, and air-dried to afford the title compound, [LCMS (Method A, Mobile Phase II) RT=3.84 min, MH+ 431].

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. customair-dried

Sources & evidence

ORD record
ord-281100eedad74a6a952bfc7cb108755d
Source dataset
uspto-grants-2011_08
Patent number
US08003806B2

Reaction notes

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