Sodium Carbonate → HCID 70168342, compound

HRID 277322Notes

Reaction equation

HRID 277322 reaction equation
[F:1][C@@H:2]1[C@H:9](C)[O:8][C@@H:5]([O:6]C)[C@H:4](O)[C@@H:3]1O.[C:13]([O-])([O-])=O.[Na+].[Na+].[C:19]([O:22][C:23](=[O:25])[CH3:24])(=[O:21])[CH3:20].[C:26]([O:29]CC)(=[O:28])[CH3:27]>S(=O)(=O)(O)O>[F:1][C@@H:2]1[C@H:3]([CH3:13])[O:21][CH:19]([O:22][C:23](=[O:25])[CH3:24])[C@H:20]([O:29][C:26](=[O:28])[CH3:27])[C@@H:9]1[O:8][C:5](=[O:6])[CH3:4]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 70169809Methyl 4,6-dideoxy-4-fluoro-α-L-talopyranosideHCID 86757863HCID 86757863, compound

Product 1

HCID 70168342HCID 70168342, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Methyl 4,6-dideoxy-4-fluoro-α-L-talopyranoside (WP 351) (33 g, 0.183 mol) was dissolved in a mixture of acetic anhydride/ethyl acetate (1:1 v/v, 600 mL) and sulfuric acid (1.5 mL) was added. After 2 hours, the reaction was finished and the reaction mixture was neutralized with a mixture of ice/NaHCO3/aq. Na2CO3 over 4 h. The product was extracted with ethyl acetate and dried with anhydrous Na2SO4. After evaporation of the solvents, the oily residue was dried under reduced pressure to give a crude crystallizing product, which was then purified by crystallization from ethyl ether to give 4,6-dideoxy-4-fluoro-1,2,3-tri-O-acetyl-L-talopyranose (WP 556) (FIG. 3) (50 g, 0.171 mol). Yield: 94%.

Workup

  1. additionwas added
  2. extractionThe product was extracted with ethyl acetate
  3. dry with materialdried with anhydrous Na2SO4
  4. customAfter evaporation of the solvents
  5. customthe oily residue was dried under reduced pressure
  6. customto give a crude
  7. customcrystallizing product, which
  8. customwas then purified by crystallization from ethyl ether

Sources & evidence

ORD record
ord-cced8d6e15784a4c82176db4e0cbd718
Source dataset
uspto-grants-2002_03
Patent number
US06355784B1

Reaction notes

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