Omeprazole → 3-Chlorobenzoic Acid

HRID 1387678Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1387678
COC1C=CC2NC(S(CC3C(C)=C(OC)C(C)=CN=3)=O)=NC=2C=1.N1C=CC=CC=1CS(C1NC2C=CC=CC=2N=1)=O.N1C=CC=CC=1CSC1NC2C=CC=CC=2N=1.[Cl:60][C:61]1[CH:62]=[C:63]([CH:68]=[CH:69][CH:70]=1)[C:64]([O:66]O)=[O:65]>C(Cl)(Cl)Cl>[Cl:60][C:61]1[CH:62]=[C:63]([CH:68]=[CH:69][CH:70]=1)[C:64]([OH:66])=[O:65]

Komponenten

6

Edukt 4

HCID 4594OmeprazoleHCID 70297m-Chloroperbenzoic acidHCID 72171TimoprazoleHCID 6839492-((pyridin-2-ylmethyl)thio)-1H-benzo[d]imidazole

Produkt 1

HCID 4473-Chlorobenzoic Acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

5-methoxy-2-[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl- 1H-benzimidazole (omeprazole) was disclosed for the first time in U.S. Pat. No. 4,255,431. In the process of preparing 2-(2-pyridylmethylsulfinyl)benzimidazole compounds there is mentioned an oxidation of corresponding 2-(2-pyridylmethylthio)benzimidazole compounds with 3-chloroperoxybenzoic acid in a chloroform solution under stirring and cooling at a temperature under 5° C. 3-chlorobenzoic acid formed is then filtered off, the filtrate is diluted with methylene chloride, washed with Na2CO3, dried with Na2SO4, evaporated in vacuo and the residue is crystallized under addition of CH3CN. Since omeprazole is unstable in an acidic medium, the cooling of the reaction mixture to 5° C. is necessary to prevent a decomposition of the omeprazole formed.

Quellen und Nachweise

ORD-Eintrag
ord-870ea6c530364bcab1c884964fa1820a
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06268502B1

Notizen zur Reaktion

Wird geladen…