3-(1H-imidazol-1-yl)benzoic acid → tert-Butyl 3-(3-(1H-imidazol-1-yl)phenyl)-3-oxopropanoate

HRID 859347Notes

Reaction equation

HRID 859347 reaction equation
[N:1]1([C:6]2[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=2)[C:9]([O:11]C)=O)[CH:5]=[CH:4][N:3]=[CH:2]1.N1(C2C=C(C=CC=2)C(O)=O)C=CN=C1.[C:30]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])(=[O:32])[CH3:31].[Li]>OS(O)(=O)=O.CO>[C:34]([O:33][C:30](=[O:32])[CH2:31][C:9]([C:8]1[CH:13]=[CH:14][CH:15]=[C:6]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)[CH:7]=1)=[O:11])([CH3:37])([CH3:36])[CH3:35]

Participants

5

Reactant 3

HCID 27955443-(1H-imidazol-1-yl)benzoic acidHCID 22224641Methyl 3-(1H-imidazol-1-YL)benzoateHCID 86586795Lithium Tert-butyl Acetate

Product 1

HCID 69592789tert-Butyl 3-(3-(1H-imidazol-1-yl)phenyl)-3-oxopropanoate

Reagents, catalysts & solvents 1

HCID 18363649Sulfuric acid methanolSolvent

Procedure

Prepared from methyl 3-(1H-imidazol-1-yl)benzoate [prepared from 3-(1H-imidazol-1-yl)benzoic acid (J. Med. Chem. 1987, 30, 1342; CAS-No. [108035-47-8] by refluxing in conc. H2SO4/MeOH] by treatment with lithium tert.-butyl acetate according to general procedure H (method b). Obtained as an orange-brown oil.

Workup

  1. customObtained as an orange-brown oil

Sources & evidence

ORD record
ord-2016da0430264a6585ca86904c3bf78b
Source dataset
uspto-grants-2006_12
Patent number
US07151098B2

Reaction notes

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