Omeprazole sulfide → HCID 178488147, 화합물

HRID 275014

반응식

HRID 275014 반응식
[CH3:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([CH3:10])[C:5]([CH2:11][S:12][C:13]2[NH:17][C:16]3[CH:18]=[C:19]([O:22][CH3:23])[CH:20]=[CH:21][C:15]=3[N:14]=2)=[N:4][CH:3]=1.CO.O.C1C=C(C([O-])=[O:34])C(C(O[O-])=O)=CC=1.[Mg+2].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[N:4][C:5]([CH2:11][S+:12]([O-:34])[C:13]2[NH:14][C:15]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:16]=3[N:17]=2)=[C:6]([CH3:10])[C:7]=1[O:8][CH3:9]

참가 물질

6

반응물 4

HCID 155794Omeprazole sulfideHCID 516892Sodium BicarbonateHCID 10130449Monoperoxyphthalic Acid Magnesium SaltHCID 22242641Methanol--water (1/1)2회

생성물 1

HCID 178488147HCID 178488147, 화합물수율 92%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-10 °C

실험 절차

To a solution of 3.44 g of pyrmetazole (10.5 mmol) in 30 mL of 9:1 v/v methanol/water at -10° C. was added dropwise a solution of 3.10 g of MMPP in 30 mL of 9:1 v/v methanol/water over a 10 minute period. The reaction mixture was stirred at -10° C. for 35 minutes then poured into a mixture of 100 mL of saturated aqueous sodium bicarbonate and 40 mL of methylene chloride. The layers were separated and the aqueous layer was extracted 3 times with methylene chloride. The combined organic layers were dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under vacuum and the residue was slurried in EtOAc and the slurry stirred for 10 minutes. The solid was collected and then dried to provide 3.31 g of omeprazole (92% yield). LC analysis showed that the product was 99.5% pure.

후처리

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted 3 times with methylene chloride
  3. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under vacuum
  6. stirringthe slurry stirred for 10 minutes
  7. customThe solid was collected
  8. customdried

출처 및 근거

ORD 기록
ord-22f30f4e398e46bb82be0430fa6320ff
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05391752

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