ethyl 3-{5-[(3-aminobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate → 3-{5-[(3-Aminobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoic acid

HRID 1676049Notes

Reaction equation

HRID 1676049 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][CH:32]=1)[C:5]([NH:7][C:8]1[CH:29]=[CH:28][C:11]2[N:12]([CH:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:16][C:17]([O:19]CC)=[O:18])[CH:13]=[N:14][C:10]=2[CH:9]=1)=[O:6]>Cl>[NH2:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][CH:32]=1)[C:5]([NH:7][C:8]1[CH:29]=[CH:28][C:11]2[N:12]([CH:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:16][C:17]([OH:19])=[O:18])[CH:13]=[N:14][C:10]=2[CH:9]=1)=[O:6]

Participants

3

Reactant 1

HCID 58653680ethyl 3-{5-[(3-aminobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate

Product 1

HCID 115894023-{5-[(3-Aminobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of ethyl 3-{5-[(3-aminobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoate (50 mg, 117 μmol) in hydrochloric acid (20 mL of a 5N solution) was stirred at room temperature for 110 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=3.25 min, MH+ 401].

Workup

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

Sources & evidence

ORD record
ord-042e791c6b25401088d01940cd4664f8
Source dataset
uspto-grants-2011_08
Patent number
US08003806B2

Reaction notes

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