Sulfuric Acid → 3-(3-Imidazol-1-yl-phenyl)-3-oxo-propionic acid

HRID 859374Notes

Reaction equation

HRID 859374 reaction equation
Cl.[N:2]1([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[C:10](Cl)=[O:11])[CH:6]=[CH:5][N:4]=[CH:3]1.[N:16]1([C:21]2[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=2)[C:24]([OH:26])=[O:25])[CH:20]=[CH:19][N:18]=[CH:17]1.C[Si]([C:34]([Si](C)(C)C)([C:38]([O-:40])=O)[C:35]([O-:37])=[O:36])(C)C.[Li+].[Br-].OS(O)(=O)=O>CC#N.C(OC(C)=C)(=O)C.CCN(CC)CC>[N:2]1([C:7]2[CH:8]=[C:9]([C:10](=[O:11])[CH2:23][C:24]([OH:26])=[O:25])[CH:13]=[CH:14][CH:15]=2)[CH:6]=[CH:5][N:4]=[CH:3]1.[N:16]1([C:21]2[CH:29]=[C:28]([C:38]3[O:40][C:7]([CH3:8])([CH3:15])[O:37][C:35](=[O:36])[CH:34]=3)[CH:27]=[CH:23][CH:22]=2)[CH:20]=[CH:19][N:18]=[CH:17]1

Participants

10

Reactant 5

HCID 1118Sulfuric AcidHCID 82050Lithium BromideHCID 27955443-(1H-imidazol-1-yl)benzoic acidHCID 222245802,2-Bis(trimethylsilyl)propanedioateHCID 222245903-(1H-imidazol-1-yl)benzoyl chloride hydrochloride

Product 2

HCID 222246383-(3-Imidazol-1-yl-phenyl)-3-oxo-propionic acidHCID 222248956-(3-Imidazol-1-yl-phenyl)-2,2-dimethyl-[1,3]dioxin-4-one

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 7916Isopropenyl acetateSolventHCID 8471TriethylamineSolvent

Procedure

The 3-(3-imidazol-1-yl-phenyl)-3-oxo-propionic acid was prepared from 3-(1H-imidazol-1-yl)benzoyl chloride hydrochloride [prepared by treatment of 3-(1H-imidazol-1-yl)benzoic acid (J. Med. Chem. 1987, 30, 1342; CAS-No. [108035-47-8] with SOCl2) and bis(trimethylsilyl)malonate with Et3N and LiBr in CH3CN at 0° C. according to general procedure H (method c1). The crude material was transformed into the title compound by stirring in isopropenyl acetate and conc. H2SO4 according to general procedure J (method a). Obtained as an orange semisolid (617 g).

Sources & evidence

ORD record
ord-4d068e36655d4e59933903f0fc3bf1fe
Source dataset
uspto-grants-2006_12
Patent number
US07151098B2

Reaction notes

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