2,4,6-Trimethylpyridine → 3-Benzylsulfonylamino-6-methyl-1-(tert-butoxycarbonylmethyl)-2-pyridinone

HRID 2257113Notes

Reaction equation

HRID 2257113 reaction equation
N1C(C)=CC(C)=CC=1C.[C:10]([O:14][C:15](=[O:26])[CH2:16][N:17]1[C:22]([CH3:23])=[CH:21][CH:20]=[C:19]([NH2:24])[C:18]1=[O:25])([CH3:13])([CH3:12])[CH3:11].[CH2:27]([S:34](Cl)(=[O:36])=[O:35])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(#N)C>[C:10]([O:14][C:15](=[O:26])[CH2:16][N:17]1[C:22]([CH3:23])=[CH:21][CH:20]=[C:19]([NH:24][S:34]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)(=[O:36])=[O:35])[C:18]1=[O:25])([CH3:13])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 79532,4,6-TrimethylpyridineHCID 74740Phenylmethanesulfonyl chlorideHCID 104901153-Amino-6-methyl-1-(tert-butoxycarbonylmethyl)-2-pyridinone

Product 1

HCID 106442233-Benzylsulfonylamino-6-methyl-1-(tert-butoxycarbonylmethyl)-2-pyridinoneYield 46.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

Collidine (0.59 mL, 4.5 mmole) was added in one portion to a stirred solution of the compound of Example 94 (0.89 g, 3.7 mmole) and benzylsulfonyl chloride (0.86 g, 4.5 mmole) in acetonitrile (20 ml) cooled in an ice bath. The solution was stirred for 5 minutes at 0° C., followed by 45 min at room temperature. The reaction mixture was quenched with water, then diluted with ethyl acetate (100 mL), washed with 3% HCl (until aqueous layer is pH 1), and brine, dried over magnesium sulfate, and the solvent was removed. The residue was dissolved in methanol, concentrated to a volume of approximately 3 mL, and the product was precipitated with the addition of diethyl ether. The precipitate was filtered to give 0.67 g of the title compound. The filtrate was concentrated and chromatographed on flash silica gel using 20-67% ethyl acetate hexanes as eluent. An additional 0.20 g of the title compound was recovered. A total of 0.87 g of the title compound (59% yield) was recovered. Rf=0.29 (silica gel, 33% ethyl acetate/hexanes).

Workup

  1. temperaturecooled in an ice bath
  2. waitfollowed by 45 min at room temperature
  3. customThe reaction mixture was quenched with water
  4. additiondiluted with ethyl acetate (100 mL)
  5. washwashed with 3% HCl (until aqueous layer is pH 1), and brine
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent was removed
  8. dissolutionThe residue was dissolved in methanol
  9. concentrationconcentrated to a volume of approximately 3 mL
  10. customthe product was precipitated with the addition of diethyl ether
  11. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-a86d8efce53f49bfb256973d807de218
Source dataset
uspto-grants-1997_08
Patent number
US05656645

Reaction notes

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