Phenylmethanesulfonyl chloride → 3-Benzylsulfonylamino-6-methyl-1-(tert-butoxycarbonylmethyl)-2-pyridinone

HRID 2113043Notes

Reaction equation

HRID 2113043 reaction equation
[NH2:1][C:2]1[C:3](=[O:17])[N:4]([CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:5]([CH3:8])=[CH:6][CH:7]=1.[CH2:18]([S:25](Cl)(=[O:27])=[O:26])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>N1C=CC=CC=1.C(OCC)(=O)C>[CH2:18]([S:25]([NH:1][C:2]1[C:3](=[O:17])[N:4]([CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:5]([CH3:8])=[CH:6][CH:7]=1)(=[O:27])=[O:26])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

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

Product 1

HCID 106442233-Benzylsulfonylamino-6-methyl-1-(tert-butoxycarbonylmethyl)-2-pyridinoneYield 53.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 2-[3-amino-6-methyl-2-oxo-1(2H)-pyridinyl]acetate (3.04 g, 12.1 mmol) in pyridine (30 mL) cooled to 0° C. was added benzylsulfonylchloride (2.67 g, 15.1 mmol). While stirring of the reaction mixture the precipitate formed. After one hour the solvent was evaporated under reduced pressure and the product was partitioned between dichloromethane and 10% KHSO4 solution. The aqueous phase was extracted with dichloromethane twice. The combined organic phases were dried over a drying agent and the solvent was evaporated under reduced pressure. A brown-reddish product obtained was suspended in ethyl acetate and heated to reflux, then cooled and filtered to give 2.56 g (6.52 mmol) of a pink product.

Workup

  1. customformed
  2. customAfter one hour the solvent was evaporated under reduced pressure
  3. customthe product was partitioned between dichloromethane and 10% KHSO4 solution
  4. extractionThe aqueous phase was extracted with dichloromethane twice
  5. customThe combined organic phases were dried over a drying agent
  6. customthe solvent was evaporated under reduced pressure
  7. customA brown-reddish product obtained
  8. temperatureheated
  9. temperatureto reflux
  10. temperaturecooled
  11. filtrationfiltered

Sources & evidence

ORD record
ord-b5713e8df3874e3b94f929b391b5e269
Source dataset
uspto-grants-2009_04
Patent number
US07524871B2

Reaction notes

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