Isopropyl iodide → Travoprost

HRID 1503082

반응식

HRID 1503082 반응식
[CH2:1]1[C@@H:5]([OH:6])[C@H:4](/[CH:7]=[CH:8]/[C@@H:9]([OH:22])[CH2:10][O:11][C:12]2[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][CH:13]=2)[C@@H:3]([CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])[C@H:2]1[OH:32].C([O-])([O-])=O.[K+].[K+].[CH:39](I)([CH3:41])[CH3:40].OS([O-])(=O)=O.[Na+]>CN1CCN(C)C1=O.C(OCC)(=O)C.CCCCCC.O>[CH3:40][CH:39]([O:30][C:29]([CH2:28][CH2:27][CH2:26]/[CH:25]=[CH:24]\[CH2:23][C@@H:3]1[C@@H:4](/[CH:7]=[CH:8]/[C@@H:9]([OH:22])[CH2:10][O:11][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=2)[C@H:5]([OH:6])[CH2:1][C@@H:2]1[OH:32])=[O:31])[CH3:41]

참가 물질

9

반응물 4

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 516919Sodium BisulfateHCID 5311100Fluprostenol

생성물 1

HCID 5282226Travoprost

시약·촉매·용매 4

HCID 962Water용매HCID 66611,3-Dimethyl-2-imidazolidinone용매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
45 °C

실험 절차

463 g of Travoprost acid is dissolved in 2.3 L of 1,3-dimethylimidazolidinone (DMI), and 420 g of K2CO3 and 300 ml of isopropyl iodide are added. The reaction mixture is stirred at 45° C. After the completion of the reaction NaHSO4 solution, water, hexane and ethyl acetate are added. The mixture is shaken, then the phases are separated and the lower, aqueous phase is extracted with hexane:ethyl acetate mixture. The united organic phase is washed with water, dried over Na2SO4, the drying material is filtered off and the solution is evaporated. The product is purified by chromatography on silica gel, using diisopropyl ether, acetone, dichloromethane, isopropanol mixture as eluent.

후처리

  1. additionare added
  2. stirringThe mixture is shaken
  3. customthe phases are separated
  4. extractionthe lower, aqueous phase is extracted with hexane
  5. washThe united organic phase is washed with water
  6. dry with materialdried over Na2SO4
  7. filtrationthe drying material is filtered off
  8. customthe solution is evaporated
  9. customThe product is purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-bfd80c5b9d184c33874a0c9acec38fda
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212125B2

연결된 노트

불러오는 중…