Ethyl 3-(2-methylsulfanyl-imidazol-1-yl)-benzoate → 3-[3-(2-Methylsulfanyl-imidazol-1-yl)-phenyl]-3-oxo-propionic acid tert.-butyl ester

HRID 859356Notes

Reaction equation

HRID 859356 reaction equation
[CH3:1][S:2][C:3]1[N:4]([C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[C:11]([O:13]CC)=O)[CH:5]=[CH:6][N:7]=1.[C:19]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])(=[O:21])[CH3:20].[Li]>>[C:23]([O:22][C:19](=[O:21])[CH2:20][C:11]([C:10]1[CH:16]=[CH:17][CH:18]=[C:8]([N:4]2[CH:5]=[CH:6][N:7]=[C:3]2[S:2][CH3:1])[CH:9]=1)=[O:13])([CH3:26])([CH3:25])[CH3:24]

Participants

3

Reactant 2

HCID 22224839Ethyl 3-(2-methylsulfanyl-imidazol-1-yl)-benzoateHCID 86586795Lithium Tert-butyl Acetate

Product 1

HCID 695927603-[3-(2-Methylsulfanyl-imidazol-1-yl)-phenyl]-3-oxo-propionic acid tert.-butyl ester

Procedure

Prepared from ethyl 3-(2-methylsulfanyl-imidazol-1-yl)-benzoate [prepared by esterification of 3-(2-methoxymethylsulfanyl-imidazol-1-yl)-benzoic acid [CAS-No. 108035-46-7] with conc. H2SO4 in EtOH, followed by treatment methyl iodide and NaH in THF/DMF] by treatment with lithium tert.-butyl acetate according to general procedure H (method b). Obtained as a light brown oil (4.41 g).

Sources & evidence

ORD record
ord-3fd23eafe3e54ac3ace40c9e974f9851
Source dataset
uspto-grants-2006_12
Patent number
US07151098B2

Reaction notes

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