Ethyl 3-{6-[(3-nitrobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate → 3-{6-[(3-Nitrobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoic acid

HRID 1676063Notes

Reaction equation

HRID 1676063 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:32]=[CH:33][CH:34]=1)[C:7]([NH:9][C:10]1[CH:11]=[CH:12][C:13]2[N:17]=[CH:16][N:15]([CH:18]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:19][C:20]([O:22]CC)=[O:21])[C:14]=2[CH:31]=1)=[O:8])([O-:3])=[O:2]>Cl>[N+:1]([C:4]1[CH:5]=[C:6]([CH:32]=[CH:33][CH:34]=1)[C:7]([NH:9][C:10]1[CH:11]=[CH:12][C:13]2[N:17]=[CH:16][N:15]([CH:18]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:19][C:20]([OH:22])=[O:21])[C:14]=2[CH:31]=1)=[O:8])([O-:3])=[O:2]

Participants

3

Reactant 1

HCID 58653702Ethyl 3-{6-[(3-nitrobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate

Product 1

HCID 586536313-{6-[(3-Nitrobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of ethyl 3-{6-[(3-nitrobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate (40 mg, 87 μmol) in hydrochloric acid (20 mL of a 5N solution) was stirred at room temperature for 96 hours. The solution was then evaporated in vacuo, and the residue was purified by RP-HPLC to afford the title compound, [LCMS (Method A, Mobile Phase II) RT=3.92 min, MH+ 431].

Workup

  1. customThe solution was then evaporated in vacuo
  2. customthe residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-b164fff26a1a46c2b31bc424f8fa796e
Source dataset
uspto-grants-2011_08
Patent number
US08003806B2

Reaction notes

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