Ethyl Acetate → HCID 21873922, compound

HRID 723415Notes

Reaction equation

HRID 723415 reaction equation
[NH2:1][C:2]1[C:7]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:15][O:16][C:17](=[O:23])[C:18](=O)[CH:19](Br)[CH3:20].C(OCC)(=O)C.[OH-].[Na+]>O1CCCC1>[CH3:15][O:16][C:17]([C:18]1[N:1]=[C:2]2[C:7]([NH:8][C:9](=[O:14])[C:10]([CH3:11])([CH3:13])[CH3:12])=[CH:6][CH:5]=[CH:4][N:3]2[C:19]=1[CH3:20])=[O:23]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 11183175Methyl 3-bromo-2-oxobutanoateHCID 21873975HCID 21873975, compound

Product 1

HCID 21873922HCID 21873922, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 30 g of 2-amino-3-pivaloylaminopyridine in 300 ml of dry tetrahydrofuran are added dropwise under argon 40 g of 3-bromo-2-oxobutanoic acid methylester. The brown solution is stirred at ambient temperature for 3 d. The resulting suspension is poured onto a mixture of icewater and ethyl acetate and the mixture is neutralised by adding 10 M sodium hydroxide solution. The organic phase is separated and the aqueous layer extracted two times with ethyl acetate. The combined organic phases are washed with water and dried over anhydrous sodium sulfate. The solvent is removed in vacuo and the blue coloured residue purified by column chromatography on silica gel to yield 35 g (78%) of a light brown solid (m.p. 132° C.).

Workup

  1. customThe organic phase is separated
  2. extractionthe aqueous layer extracted two times with ethyl acetate
  3. washThe combined organic phases are washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent is removed in vacuo
  6. customthe blue coloured residue purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-0b17659bdaf24f608d1dbd63f546d41c
Source dataset
uspto-grants-2006_11
Patent number
US07141567B2

Reaction notes

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