Potassium Carbonate → HCID 44247679, compound

HRID 2204045Notes

Reaction equation

HRID 2204045 reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH3:31])=[CH:25][CH:24]=3)[CH:16]=2)[O:8][C@H:7]([O:32][CH3:33])[C@H:6]1[O:34]C(=O)C)(=O)C.C([O-])([O-])=O.[K+].[K+]>CO>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([C@H:9]2[C@H:10]([OH:11])[C@@H:5]([OH:4])[C@H:6]([OH:34])[C@@H:7]([O:32][CH3:33])[O:8]2)=[CH:16][C:17]=1[CH2:22][C:23]1[CH:24]=[CH:25][C:26]([O:29][CH2:30][CH3:31])=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 66884218HCID 66884218, compound

Product 1

HCID 44247679HCID 44247679, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Recrystallized triacetate from step C (5.98 g, 11.2 mmol) was treated with K2CO3 (7.7 g, 56 mmol) in MeOH (112 ml) with vigorous stirring for 1 hour. The reaction was filtered through celite and concentrated under vacuum. The residue was dissolved in DCM, washed with H2O and brine, dried over MgSO4, filtered, and concentrated under vacuum. The residue was passed through a plug of silica gel with 5% MeOH:CH2Cl2, concentrated under vacuum, suspended in H2O, and lyophilized to give (2S,3R,4R,5S,6S)-2-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-6-methoxy-tetrahydro-pyran-3,4,5-triol (4.37 g, 10.7 mmol, 96%) as a white solid.

Workup

  1. filtrationThe reaction was filtered through celite
  2. concentrationconcentrated under vacuum
  3. dissolutionThe residue was dissolved in DCM
  4. washwashed with H2O and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. concentrationCH2Cl2, concentrated under vacuum

Sources & evidence

ORD record
ord-f94cbdd69f5647fc89c31106c3f35522
Source dataset
uspto-grants-2016_06
Patent number
US09365602B2

Reaction notes

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