HCID 15002762, compound → HCID 15002763, compound

HRID 729175Notes

Reaction equation

HRID 729175 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[N:11]=[C:10]([CH:21]([CH3:25])[CH2:22][CH2:23][OH:24])[CH:9]=2)=[CH:4][CH:3]=1.CC(C)=[O:28].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[N:11]=[C:10]([CH:21]([CH3:25])[CH2:22][C:23]([OH:28])=[O:24])[CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 15002762HCID 15002762, compoundHCID 131709961Jones' reagent

Product 1

HCID 15002763HCID 15002763, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of compound 50 (0.65 g, 1.8 mM) in acetone (50 ml) was added Jones Reagent (1.85 ml, 3.7 mM) and the reaction stirred for 1.5 hr, the acetone decanted and the chromium residues washed exhaustively with acetone. The combined acetone layers were then evaporated in vacuo, the residue dissolved in EtOAc (100 ml), washed (H2O), dried (Na2SO4) and concentrated to give an oil which was chromatographed on Silica (EtOAc/MeOH, 30% as eluent) to afford 3-[5-(4-chlorophenyl)-1-(4-methoxyphenyl)-3-pyrazolyl]-3-methylpropanoic acid (0.62 g, 92%) as a yellow semi-solid which was used without further purification and following the procedure of Example 11 was converted to the title hydroxamic acid 51 as a yellow foam (92%); NMR (CDCl3) δ 1.50 (d, 3H, J=7Hz, C3 --CH3); MS, m/e 399 (M+).

Workup

  1. customthe acetone decanted
  2. washthe chromium residues washed exhaustively with acetone
  3. customThe combined acetone layers were then evaporated in vacuo
  4. dissolutionthe residue dissolved in EtOAc (100 ml)
  5. washwashed (H2O)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customto give an oil which
  9. customwas chromatographed on Silica (EtOAc/MeOH, 30% as eluent)

Sources & evidence

ORD record
ord-34b2efcf23754e9f80465fb557ff3d0a
Source dataset
uspto-grants-1991_09
Patent number
US05051518

Reaction notes

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