2-Oxobutanoic Acid → HCID 66939117, compound

HRID 1257383Notes

Reaction equation

HRID 1257383 reaction equation
O=[C:2]([CH2:6][CH3:7])[C:3]([OH:5])=[O:4].BrBr.[Br:10][C:11]1[CH:12]=[C:13]([C:21](=[S:23])[NH2:22])[CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=1.C(=O)([O-])O.[Na+].[CH2:29](OCC)[CH3:30]>C(O)C>[Br:10][C:11]1[CH:12]=[C:13]([C:21]2[S:23][C:6]([CH3:7])=[C:2]([C:3]([O:5][CH2:29][CH3:30])=[O:4])[N:22]=2)[CH:14]=[C:15]([C:17]([F:19])([F:20])[F:18])[CH:16]=1

Participants

7

Reactant 5

HCID 582-Oxobutanoic AcidHCID 3283Diethyl Ether2×HCID 24408BromineHCID 516892Sodium BicarbonateHCID 86650591HCID 86650591, compound

Product 1

HCID 66939117HCID 66939117, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under a nitrogen atmosphere at 0° C., to a solution (30 mL) of 2-oxobutyric acid (3.0 g, 29 mmol) in diethyl ether was slowly added dropwise a solution (20 mL) of bromine (2.6 g, 33 mmol) in diethyl ether over 30 min, and the mixture was stirred at the same temperature for 3 hr. The solvent was evaporated under reduced pressure, and to a solution (50 mL) of the residue in ethanol was added the compound (3.2 g, 11 mmol) obtained in Example 77b, and the mixture was stirred at 80° C. overnight. Saturated aqueous sodium hydrogen carbonate was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=90/10) to give a crude title compound (5.9 g) as a pale-yellow solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. stirringthe mixture was stirred at 80° C. overnight
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe obtained organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customThe resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=90/10)

Sources & evidence

ORD record
ord-f107385462de4965a4182f15880e6ab3
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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