Ethyl 3-oxovalerate → HCID 178436952, compound

HRID 2105230Notes

Reaction equation

HRID 2105230 reaction equation
[C:1]([CH2:5][C:6](OCC)=[O:7])(=O)[CH2:2][CH3:3].FC(F)(F)C(O)=O.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]1[CH:28]=[C:27]([CH:29]2[CH2:33][CH2:32][CH2:31][N:30]2[C:34](=[NH:36])[NH2:35])[O:26][N:25]=1.C[O-].[Na+]>C(O)CCC>[CH2:2]([C:1]1[N:35]=[C:34]([N:30]2[CH2:31][CH2:32][CH2:33][CH:29]2[C:27]2[O:26][N:25]=[C:24]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][N:18]=3)[CH:28]=2)[N:36]=[C:6]([OH:7])[CH:5]=1)[CH3:3]

Participants

5

Reactant 3

HCID 78656Ethyl 3-oxovalerateHCID 10942334Sodium MethoxideHCID 68813895HCID 68813895, compound

Product 1

HCID 178436952HCID 178436952, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of ethyl propionylacetate (350 mg, 2.4 mmol), 2-[3-(pyrid-2-yl)isoxazol-5-yl]pyrrolidine-1-carboximidamide trifluoroacetate salt (Method 38) (901 mg, 2.43 mmol), sodium methoxide (144 mg, 7.7 mmol), in butanol (10 ml) was heated at 120° C. for 18 hours. The mixture was allowed to cool and poured directly on to an isolute SCX2 ion exchange column. The column was eluted with DCM/methanol (4:1) to remove neutrals and then with 7M methanolic ammonia to elute the product. The solvent was evaporated and the residue purified by chromatography on silica gel eluting with DCM/methanol (98:2 increasing in polarity to 95:5) to give the title compound (360 mg, 46%).

Workup

  1. temperatureto cool
  2. washThe column was eluted with DCM/methanol (4:1)
  3. customto remove neutrals
  4. washwith 7M methanolic ammonia to elute the product
  5. customThe solvent was evaporated
  6. customthe residue purified by chromatography on silica gel eluting with DCM/methanol (98:2 increasing in polarity to 95:5)

Sources & evidence

ORD record
ord-f193643116e14bfe81be6a50995f31b0
Source dataset
uspto-grants-2009_08
Patent number
US07579349B2

Reaction notes

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