Sodium Methoxide → HCID 54486594, compound

HRID 634881Notes

Reaction equation

HRID 634881 reaction equation
C([O:4][C@@H:5]1[C@H:18]([O:19]C(=O)C)[C@H:17]([CH3:23])[O:16][C@H:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C@@H:6]1[F:24])(=O)C.C[O-].[Na+]>CO>[F:24][C@@H:6]1[C@H:5]([OH:4])[C@H:18]([OH:19])[C@H:17]([CH3:23])[O:16][C@@H:7]1[O:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 15907794HCID 15907794, compound

Product 1

HCID 54486594HCID 54486594, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Benzyl 3,4-di-O-acetyl-2,6-dideoxy-2-fluoro-β-L-talopyranoside (1.66 g) obtained in Example 1-(1) above was suspended in 50 ml of anhydrous methanol. The resulting suspension was added with 0.5 ml of a solution of 4.9 M sodium methoxide in methanol and then stirred at room temperature for 30 minutes to effect the reaction intended. The homogenous reaction solution so obtained was neutralized by addition thereto of an ion-exchange resin, Dowex 50 W×2 (H+-form) and then filtered to remove the resin therefrom. The filtrate obtained was concentrated to a small volume and the concentrated solution was allowed to stand at −10° C. and the deposited needles were separated by filtration, affording 1.11 g (yield 89%) of the titled Compound (4).

Workup

  1. customThe homogenous reaction solution so obtained
  2. additionwas neutralized by addition
  3. filtrationof an ion-exchange resin, Dowex 50 W×2 (H+-form) and then filtered
  4. customto remove the resin
  5. customThe filtrate obtained
  6. concentrationwas concentrated to a small volume
  7. customto stand at −10° C.
  8. customthe deposited needles were separated by filtration

Sources & evidence

ORD record
ord-157ff1ce9a9f442ca46d776a67abf48f
Source dataset
uspto-grants-2001_02
Patent number
US06184365B2

Reaction notes

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