Water → Methyl 3,23-O-isopropylideneasiatate

HRID 355666Notes

Reaction equation

HRID 355666 reaction equation
[CH3:1][C@H:2]1[C@H:30]([CH3:31])[C@@H:29]2[C@@:5]([C:33]([O:35][CH3:36])=[O:34])([CH2:6][CH2:7][C@@:8]3([CH3:32])[C@:13]4([CH3:28])[CH2:14][CH2:15][C@H:16]5[C@@:21]([CH2:23][OH:24])([CH3:22])[C@@H:20]([OH:25])[C@H:19]([OH:26])[CH2:18][C@:17]5([CH3:27])[C@H:12]4[CH2:11][CH:10]=[C:9]32)[CH2:4][CH2:3]1.[C:37]1(C)[CH:42]=CC(S(O)(=O)=O)=C[CH:38]=1.O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][C@H:2]1[C@H:30]([CH3:31])[C@@H:29]2[C@@:5]([C:33]([O:35][CH3:36])=[O:34])([CH2:6][CH2:7][C@@:8]3([CH3:32])[C@:13]4([CH3:28])[CH2:14][CH2:15][C@H:16]5[C@:21]6([CH3:22])[CH2:23][O:24][C:37]([CH3:42])([CH3:38])[O:25][C@H:20]6[C@H:19]([OH:26])[CH2:18][C@:17]5([CH3:27])[C@H:12]4[CH2:11][CH:10]=[C:9]32)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 11430Potassium CarbonateHCID 21672634HCID 21672634, compound

Product 1

HCID 72697328Methyl 3,23-O-isopropylideneasiatateYield 60.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl asiatate 2 (27.7 mg, 0.055 mmole) was dissolved in anhydrous acetone (3 ml), added with p-toluenesulfonic acid (27.7 mg) and then refluxed. Water was added to the reaction mixture, and the solution was neutralized with 5% potassium carbonate and then extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The was chromatographed with benzene and ethyl acetate (3:2) to give pure desired compound (18 mg, 60%).

Workup

  1. temperaturerefluxed
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe was chromatographed with benzene and ethyl acetate (3:2)

Sources & evidence

ORD record
ord-6b3657e080484062b71460ba733a7f24
Source dataset
uspto-grants-1998_11
Patent number
US05834437

Reaction notes

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