Benzoic acid, 3-isothiocyanato- → 3-[3-(4-Methyl-imidazol-1-yl)-phenyl]-3-oxo-propionic acid tert.-butyl ester

HRID 1635226

Reaktionsgleichung

Reaktionsgleichung von HRID 1635226
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=2)[C:10]([O:12]C)=O)[CH:6]=1.N(C1C=C(C=CC=1)C(O)=O)=C=S.COC(OC)C(N)C.[C:37]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])(=[O:39])[CH3:38].[Li]>OS(O)(=O)=O.CO>[C:41]([O:40][C:37](=[O:39])[CH2:38][C:10]([C:9]1[CH:14]=[CH:15][CH:16]=[C:7]([N:5]2[CH:6]=[C:2]([CH3:1])[N:3]=[CH:4]2)[CH:8]=1)=[O:12])([CH3:44])([CH3:43])[CH3:42]

Komponenten

6

Edukt 4

HCID 75046Benzoic acid, 3-isothiocyanato-HCID 936582,2-Dimethoxy-1-methylethylamineHCID 22224935Methyl 3-(4-methyl-1H-imidazol-1-YL)benzoateHCID 86586795Lithium Tert-butyl Acetate

Produkt 1

HCID 695927773-[3-(4-Methyl-imidazol-1-yl)-phenyl]-3-oxo-propionic acid tert.-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 18363649Sulfuric acid methanolLösungsmittel

Versuchsvorschrift

Prepared from methyl 3-(4-methyl-imidazol-1-yl)-benzoate [prepared the corresponding acid from 3-isothiocyanatobenzoic acid and 2-aminopropionaldehyde dimethyl acetal according to J. Med. Chem. 1987, 30, 1342, followed by refluxing in conc. H2SO4/MeOH] by treatment with lithium tert.-butyl acetate according to general procedure H (method b). Obtained as a yellow-brown oil (10.69 g).

Quellen und Nachweise

ORD-Eintrag
ord-6ebc61048ac04d5194ba46582fac5e4f
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06509328B1

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