Omeprazole → 3-Chlorobenzoic Acid

HRID 1387678

반응식

HRID 1387678 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

HCID 4473-Chlorobenzoic Acid

시약·촉매·용매 1

HCID 6212Chloroform용매

반응 조건

온도
5 °C

실험 절차

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.

출처 및 근거

ORD 기록
ord-870ea6c530364bcab1c884964fa1820a
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06268502B1

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