Hydrochloric Acid → 3-(3-Methylphenylsulfonyl)amino-6-methyl-1-carboxymethyl-2-pyridinone

HRID 413451Notes

Reaction equation

HRID 413451 reaction equation
Cl.[CH3:2][C:3]1[CH:4]=[C:5]([S:9]([NH:12][C:13]2[C:14](=[O:28])[N:15]([CH2:20][C:21]([O:23]C(C)(C)C)=[O:22])[C:16]([CH3:19])=[CH:17][CH:18]=2)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1>C(OCC)(=O)C>[CH3:2][C:3]1[CH:4]=[C:5]([S:9]([NH:12][C:13]2[C:14](=[O:28])[N:15]([CH2:20][C:21]([OH:23])=[O:22])[C:16]([CH3:19])=[CH:17][CH:18]=2)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 120720263-(3-Methylphenylsulfonyl)amino-6-methyl-1-(tert-butoxycarbonylmethyl)-2-pyridinone

Product 1

HCID 120720273-(3-Methylphenylsulfonyl)amino-6-methyl-1-carboxymethyl-2-pyridinoneYield 80%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

HCl gas was bubbled through a stirred suspension of 3-(3-methylphenylsulfonyl)amino-6-methyl-1-(tert-butoxycarbonylmethyl)-2-pyridinone (2.0 g, 5.09 mmol), as prepared in the preceding step, in ethyl acetate (50 mL) at 0° C. until a solution was formed. After warming to room temperature over 2 h, a thick suspension was formed. The mixture was degassed with nitrogen and filtered to give the title compound as a white solid (1.36 g, 80%). 1H-NMR (300 MHz, DMSO-d6) δ9.38 (s, 1H), 7.62 (m, 2H), 7.41 (m, 2H), 7.25 (d, 1H, J=8 Hz), 6.09 (d, 1H, J=8 Hz), 4.67 (s, 2H), 2.35 (s, 3H), 2.20 (s, 3H).

Workup

  1. customwas formed
  2. customa thick suspension was formed
  3. customThe mixture was degassed with nitrogen
  4. filtrationfiltered

Sources & evidence

ORD record
ord-23dcaee43dad4da68601f613d7b5c9a8
Source dataset
uspto-grants-2003_05
Patent number
US06566379B1

Reaction notes

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