HCID 178450726, compound → 4-{2-phenyl-5-[2-(1H-tetrazol-5-yl)-ethyl]-pyrrol-1-yl}-benzoic acid

HRID 1261410Notes

Reaction equation

HRID 1261410 reaction equation
C([O:5][C:6](=[O:31])[C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17]([CH2:18][CH2:19][C:20]3[NH:24][N:23]=[N:22][N:21]=3)=[CH:16][CH:15]=[C:14]2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:9][CH:8]=1)(C)(C)C>C(O)=O>[C:25]1([C:14]2[N:13]([C:10]3[CH:9]=[CH:8][C:7]([C:6]([OH:31])=[O:5])=[CH:12][CH:11]=3)[C:17]([CH2:18][CH2:19][C:20]3[NH:24][N:23]=[N:22][N:21]=3)=[CH:16][CH:15]=2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

3

Reactant 1

HCID 178450726HCID 178450726, compound

Product 1

HCID 1785244444-{2-phenyl-5-[2-(1H-tetrazol-5-yl)-ethyl]-pyrrol-1-yl}-benzoic acidYield 32.4%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 4-{2-phenyl-5-[2-(1h-tetrazol-5-yl)ethyl]-pyrrol-1-yl}-benzoic acid tert-butyl ester (1.34 mmol, 1.0 eq) in formic acid (4.2 ml) was stirred at room temperature for 42 hours. The solvent was evaporated in vacuo and the residue purified by prep HPLC. Removal of the solvent in vacuo yielded 156 mg desired product 4-{2-phenyl-5-[2-(1H-tetrazol-5-yl)ethyl]-pyrrol-1-yl}-benzoic acid (32%) and 180 mg byproduct in which the t-butyl group had migrated to the tetrazole ring (37%).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue purified by prep HPLC
  3. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-0832f0062e5a40ae95f4118f138bfd88
Source dataset
uspto-grants-2013_06
Patent number
US08470857B2

Reaction notes

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