Acetic Acid → HCID 131726891, compound

HRID 2224017Notes

Reaction equation

HRID 2224017 reaction equation
C(O)(=O)C.O1CCCC1.FC(F)(F)C(O)=O.[Na:17].[Si]([O:25][C@@H:26]1[C@@H:31]([O:32][Si](C(C)(C)C)(C)C)[C@H:30]([O:40][Si](C(C)(C)C)(C)C)[C@@H:29]([CH2:48][S:49]([OH:52])(=[O:51])=[O:50])[O:28][C@@H:27]1[O:53][CH2:54][CH:55]([OH:77])[CH2:56][O:57][C:58](=[O:76])[CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65]/[CH:66]=[CH:67]\[CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH3:75])(C(C)(C)C)(C)C>O>[Na:17].[S:49]([CH2:48][C@H:29]1[O:28][C@H:27]([O:53][CH2:54][CH:55]([OH:77])[CH2:56][O:57][C:58](=[O:76])[CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65]/[CH:66]=[CH:67]\[CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH3:75])[C@H:26]([OH:25])[C@@H:31]([OH:32])[C@@H:30]1[OH:40])([OH:52])(=[O:50])=[O:51]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6422Trifluoroacetic acidHCID 8028TetrahydrofuranHCID 131726892HCID 131726892, compound

Product 1

HCID 131726891HCID 131726891, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into 7 mL of a solution of acetic acid, tetrahydrofuran, trifluoroacetic acid and water (3:1:0.4:1), 358.4 mg (378 μmol) of the compound (X) was dissolved. The solution was reacted at room temperature for 16 hours while stirring, and the reaction mixture was extracted with ethyl acetate (3×10 mL). The. organic layers were combined, washed with brine (2×20 mL), dried over anhydrous sodium sulfate, filtered, concentrated in vacuo, and purified by silica gel flash chromatography (dichloromethane methanol=10:1→dichloromethane:methanol:water=65:25:4) (yield: 138.1 mg (229 μmol), recovery: 62.7%).

Workup

  1. customThe solution was reacted at room temperature for 16 hours
  2. extractionthe reaction mixture was extracted with ethyl acetate (3×10 mL)
  3. washwashed with brine (2×20 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by silica gel flash chromatography (dichloromethane methanol=10:1→dichloromethane:methanol:water=65:25:4) (yield: 138.1 mg (229 μmol), recovery: 62.7%)

Sources & evidence

ORD record
ord-a8edfb6fd930475ba1aaf63e84e628b3
Source dataset
uspto-grants-2008_05
Patent number
US07378398B2

Reaction notes

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