m-Chloroperbenzoic acid → HCID 66562085, compound

HRID 512095Notes

Reaction equation

HRID 512095 reaction equation
C([O:8][C:9]1[C:14]([O:15][CH3:16])=[C:13]([CH3:17])[N:12]=[C:11]([CH3:18])[C:10]=1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])C1C=CC=CC=1.C1C=C(Cl)C=C(C(OO)=[O:34])C=1>C(Cl)Cl.CCO.[Pd]>[CH2:19]([C:10]1[C:9](=[O:8])[C:14]([O:15][CH3:16])=[C:13]([CH3:17])[N:12]([OH:34])[C:11]=1[CH3:18])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 70818741HCID 70818741, compound

Product 1

HCID 66562085HCID 66562085, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 20 (19 mg, 0.66 mmol) and mCPBA (125 mg, 0.72 mmol) in anhydrous CH2Cl2 (2 mL) was stirred at 0° C. for 1 hr under argon atmosphere, the solution was washed with aqueous NaHCO3 dried over anhydrous MgSO4 and concentrated under diminished pressure to afford a crude residue. The residue was dissolved in EtOH, Pd/C was added and after applying an H2 atmosphere (1 bar), the solution was stirred at room temp for 30 min, After filtration through celite, which was thoroughly washed with EtOH, the filtrate was concentrated under diminished pressure and purified by chromatography on a silica gel column. Elution with 20:1 ethyl acetate/methanol gave 3-heptyl-1-hydroxy-5-methoxy-2,6-dimethylpyridin-4(1H)-one (CPD-5) as a light yellow oil; yield 9 mg (61%); silica gel TLC Rf 0.25 (3:1 ethyl acetate/methanol); 1H NMR (CDCl3) δ 0.84-0.89 (m, 3H), 1.24-1.35 (m, 10H), 2.45 (s, 3H), 2.50 (s, 3H) 2.63-2.67 (m, 2H) and 3.74 (s, 3H).

Workup

  1. washthe solution was washed with aqueous NaHCO3
  2. dry with materialdried over anhydrous MgSO4
  3. concentrationconcentrated under diminished pressure
  4. customto afford a crude residue
  5. filtrationAfter filtration through celite, which
  6. washwas thoroughly washed with EtOH
  7. concentrationthe filtrate was concentrated under diminished pressure
  8. custompurified by chromatography on a silica gel column
  9. washElution with 20:1 ethyl acetate/methanol

Sources & evidence

ORD record
ord-5eaa1ccfb34f479f956080bbeb4d94bc
Source dataset
uspto-grants-2015_08
Patent number
US09102626B2

Reaction notes

Loading…