Cyclohexylmethane sulfonyl chloride → [3-(Cyclohexylmethylsulfonylamino)-6-methyl-2-oxo-1,2-dihydropyridinyl]-acetic acid

HRID 636974

Reaction equation

HRID 636974 reaction equation
[NH2:1][C:2]1[C:3](=[O:17])[N:4]([CH2:9][C:10]([O:12]C(C)(C)C)=[O:11])[C:5]([CH3:8])=[CH:6][CH:7]=1.[CH:18]1([CH2:24][S:25](Cl)(=[O:27])=[O:26])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>>[CH:18]1([CH2:24][S:25]([NH:1][C:2]2[C:3](=[O:17])[N:4]([CH2:9][C:10]([OH:12])=[O:11])[C:5]([CH3:8])=[CH:6][CH:7]=2)(=[O:27])=[O:26])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

3

Reactant 2

HCID 3871475Cyclohexylmethane sulfonyl chlorideHCID 104901153-Amino-6-methyl-1-(tert-butoxycarbonylmethyl)-2-pyridinone

Product 1

HCID 57104637[3-(Cyclohexylmethylsulfonylamino)-6-methyl-2-oxo-1,2-dihydropyridinyl]-acetic acid

Procedure

To a stirred solution of 0.71 g of tert-butyl [3-amino-6-methyl-2-oxo-1,2-dihydropyridinyl]-acetate (WO 97/01338) at 0° C. under a nitrogen atmosphere was added 0.60 mL cyclohexylmethanesulfonyl chloride (J. F. King et al J. Am. Chem. Soc. 114, 1743 (1992)). After stirring at room temperature for 3 hours the reaction mixture was concentrated. The residue was dissolved in ethyl acetate, washed successively with 0.1 N hydrochloric acid, water and brine, dried over sodium sulphate and concentrated. The residue was dissolved in a mixture of 0.2 mL water and 1.8 mL trifluoroacetic acid. After stirring at room temperature for 4 h, water and ethyl acetate were added. The organic layer was separated, washed twice with 0.1 N hydrochloric acid, dried over sodium sulphate and concentrated. The solid residue was washed with a cold dichloromethane/diethyl ether mixture to give 0.72 g of the title compound.

Workup

  1. concentrationwas concentrated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed successively with 0.1 N hydrochloric acid, water and brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in a mixture of 0.2 mL water and 1.8 mL trifluoroacetic acid
  7. stirringAfter stirring at room temperature for 4 h
  8. additionwater and ethyl acetate were added
  9. customThe organic layer was separated
  10. washwashed twice with 0.1 N hydrochloric acid
  11. dry with materialdried over sodium sulphate
  12. concentrationconcentrated
  13. washThe solid residue was washed with a cold dichloromethane/diethyl ether mixture

Sources & evidence

ORD record
ord-5f4480e641094696be6143e9f1d89091
Source dataset
uspto-grants-2001_02
Patent number
US06194409B1

Linked notes

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