Acetic Acid → HCID 86714025, compound

HRID 1410296Notes

Reaction equation

HRID 1410296 reaction equation
C([O:4][C@H:5]1[C@H:10]([O:11]C(=O)C)[C@@H:9]([O:15]C(=O)C)[C@H:8]([C:19]2[CH:24]=[C:23]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH3:34])=[CH:28][CH:27]=3)[C:22]([Cl:35])=[CH:21][C:20]=2[O:36][CH2:37][CH:38]=[CH2:39])[O:7][C@@H:6]1[CH2:40][O:41]C(=O)C)(=O)C.C[O-].[Na+].C(O)(=O)C>CO>[CH2:37]([O:36][C:20]1[CH:21]=[C:22]([Cl:35])[C:23]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH3:34])=[CH:28][CH:27]=2)=[CH:24][C:19]=1[C@H:8]1[C@H:9]([OH:15])[C@@H:10]([OH:11])[C@H:5]([OH:4])[C@@H:6]([CH2:40][OH:41])[O:7]1)[CH:38]=[CH2:39]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 86728583HCID 86728583, compound

Product 1

HCID 86714025HCID 86714025, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(2-(allyloxy)-4-chloro-5-(4-ethoxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (12, 4 g, 6.32 mmol) from Step 1 in methanol (90 mL) was added sodium methoxide (25% in methanol, 9 mL) and the reaction mixture was stirred at ambient temperature for 5 h. The solution was cooled to 0° C. prior to neutralizing with acetic acid (4.5 mL). After removal of organic volatiles under reduced pressure, the residue was diluted with ethyl acetate and water. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with sodium hydrogen carbonate and brine, dried over magnesium sulfate, filtered and concentrated in vacuo to yield the title compound (13) as a white solid which was used without further purification.

Workup

  1. temperatureThe solution was cooled to 0° C.
  2. customAfter removal of organic volatiles under reduced pressure
  3. additionthe residue was diluted with ethyl acetate and water
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washThe combined organic layers were washed with sodium hydrogen carbonate and brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1e059fef004f4e2ba94434973a419d04
Source dataset
uspto-grants-2014_12
Patent number
US08921412B2

Reaction notes

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