Potassium Acetate → HCID 86592451, compound

HRID 430937Notes

Reaction equation

HRID 430937 reaction equation
Br[C@H:2]([C@H:7]([CH2:9]Br)[OH:8])[C:3]([O:5][CH3:6])=[O:4].[C:11]([O-:14])(=[O:13])[CH3:12].[K+]>CN(C)C=O.C(OCC)(=O)C.[I-].[K+]>[C:11]([O:14][CH2:9][C@@H:7]1[O:8][C@@H:2]1[C:3]([O:5][CH3:6])=[O:4])(=[O:13])[CH3:12]

Participants

6

Reactant 2

HCID 517044Potassium AcetateHCID 14168308HCID 14168308, compound

Product 1

HCID 86592451HCID 86592451, compoundYield 99.3%

Reagents, catalysts & solvents 3

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
52.5 °C

Procedure

The general procedure of Manchand, et. al. (Manchand, et al., 1988) is employed. Methyl 2,4-dibromo-2,4-dideoxy-L-threonate (131 g, 474 mmol) is added to a stirred solution of potassium acetate (102 g, 1.04 mol) and potassium iodide (3.94 g, 23.8 mmol) in dimethyl formamide (500 mL). This mixture is stirred under nitrogen gas at 50-55° C. for 4 hours and overnight at room temperature. The reaction mixture is diluted with ethyl acetate (1 L) and filtered. The filter cake is washed with ethyl acetate (250 mL). The combined ethyl acetate portion is washed with saturated sodium bicarbonate solution (500 mL) and saturated brine (2×500 mL) and dried over magnesium sulfate. The solvent is removed to yield the title compound as a dark oil (82.0 g, 99% theoretical yield).

Workup

  1. filtrationfiltered
  2. washThe filter cake is washed with ethyl acetate (250 mL)
  3. washThe combined ethyl acetate portion is washed with saturated sodium bicarbonate solution (500 mL) and saturated brine (2×500 mL)
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent is removed

Sources & evidence

ORD record
ord-a7678da6b6594f30b544b3cd2426c191
Source dataset
uspto-grants-2003_12
Patent number
US06656917B1

Reaction notes

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