Acetic Acid → HCID 86728587, compound

HRID 1410300Notes

Reaction equation

HRID 1410300 reaction equation
C([O:4][CH2:5][C@@H:6]1[C@@H:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@H:10]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@@H:9]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@H:8]([C:36]2[CH:41]=[C:40]([CH2:42][C:43]3[CH:48]=[CH:47][C:46]([O:49][CH2:50][CH3:51])=[CH:45][CH:44]=3)[C:39]([Cl:52])=[CH:38][C:37]=2[O:53][CH2:54][CH:55]=[CH2:56])[O:7]1)(=O)C.C[O-].[Na+].C(O)(=O)C>CO>[CH2:54]([O:53][C:37]1[CH:38]=[C:39]([Cl:52])[C:40]([CH2:42][C:43]2[CH:44]=[CH:45][C:46]([O:49][CH2:50][CH3:51])=[CH:47][CH:48]=2)=[CH:41][C:36]=1[C@@H:8]1[O:7][C@H:6]([CH2:5][OH:4])[C@@H:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@H:10]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C@H:9]1[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH:55]=[CH2:56]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 86728586HCID 86728586, compound

Product 1

HCID 86728587HCID 86728587, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ((2R,3R,4R,5S,6S)-6-(2-(allyloxy)-4-chloro-5-(4-ethoxybenzyl)phenyl)-3,4,5-tris(benzyloxy)tetrahydro-2H-pyran-2-yl)methyl acetate (20, 7.8 g, 10 mmol) from Step 4 in methanol (130 mL) was added sodium methoxide (25% in methanol, 13 mL) and the reaction mixture was vigorously stirred at ambient temperature for 5 h. The solution was cooled to 0° C. prior to neutralizing with acetic acid (6.5 mL). After removal of organic volatiles under reduced pressure, the residue was diluted 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. The crude residue was purified on Biotage® purification apparatus (silica gel, 5 to 30% tetrahydrofuran in hexanes) to yield the title compound (21, 7.2 g, 9.8 mmol, 98%) as a white solid.

Workup

  1. temperatureThe solution was cooled to 0° C.
  2. customAfter removal of organic volatiles under reduced pressure
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layers were washed with sodium hydrogen carbonate and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was purified on Biotage® purification apparatus (silica gel, 5 to 30% tetrahydrofuran in hexanes)

Sources & evidence

ORD record
ord-0e9b3aed3c7747c9883363fe04b92487
Source dataset
uspto-grants-2014_12
Patent number
US08921412B2

Reaction notes

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