Isopropyl iodide → Travoprost

HRID 1503082

Reaction equation

HRID 1503082 reaction equation
[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]

Participants

9

Reactant 4

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

Product 1

HCID 5282226Travoprost

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 66611,3-Dimethyl-2-imidazolidinoneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-bfd80c5b9d184c33874a0c9acec38fda
Source dataset
uspto-grants-2015_12
Patent number
US09212125B2

Linked notes

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