Omeprazole sulfide → HCID 178488147、化合物

HRID 275014

反応式

HRID 275014 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 178488147HCID 178488147、化合物収率 92%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-10 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-22f30f4e398e46bb82be0430fa6320ff
出典データセット
uspto-grants-1995_02
特許番号
US05391752

関連ノート

読み込み中…