Acetic Acid → HCID 68590601, compound

HRID 1517542Notes

Reaction equation

HRID 1517542 reaction equation
[C:1]([C:5]1[C:6]([O:22][CH3:23])=[CH:7][C:8]([CH2:19][S:20][CH3:21])=[C:9]([C:11]2[C:12]([O:17]C)=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].Br.CC(O)=O.C([O-])([O-])=O.[K+].[K+]>O>[C:1]([C:5]1[C:6]([O:22][CH3:23])=[CH:7][C:8]([CH2:19][S:20][CH3:21])=[C:9]([C:11]2[C:12](=[O:17])[NH:13][CH:14]=[CH:15][CH:16]=2)[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 11430Potassium CarbonateHCID 67372768HCID 67372768, compound

Product 1

HCID 68590601HCID 68590601, compoundYield 20.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

step 3—A mixture of 82 (30 mg), 48% HBr (50 μL) and HOAc (2 mL) in a sealed tube was heated overnight at 70° C. The reaction mixture was cooled to RT, carefully poured into water and neutralized with K2CO3 then extracted with EtOAc. The organic extract was washed with brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified on a preparative SiO2 TLC developed with 8% MeOH/DCM to afford 6 mg of 3-(5-tert-butyl-4-methoxy-2-methylsulfanylmethyl-phenyl)-1H-pyridin-2-one (84) as a white solid. The title compound can be prepared by oxidation of 84 with MCPBA which afford the sulfone I-15 directly.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. extractionthen extracted with EtOAc
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was purified on a preparative SiO2 TLC

Sources & evidence

ORD record
ord-5ae39a0b4cc74e23ab3565484c050db5
Source dataset
uspto-grants-2012_07
Patent number
US08232271B2

Reaction notes

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