Hydrochloric Acid → 3-Benzylsulfonylamino-6-methyl-1-carboxymethyl-2-pyridinone

HRID 413439Notes

Reaction equation

HRID 413439 reaction equation
Cl.[CH2:2]([S:9]([NH:12][C:13]1[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]=1)(=[O:11])=[O:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(OCC)(=O)C>[CH2:2]([S:9]([NH:12][C:13]1[C:14](=[O:28])[N:15]([CH2:20][C:21]([OH:23])=[O:22])[C:16]([CH3:19])=[CH:17][CH:18]=1)(=[O:11])=[O:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 106442233-Benzylsulfonylamino-6-methyl-1-(tert-butoxycarbonylmethyl)-2-pyridinone

Product 1

HCID 154582213-Benzylsulfonylamino-6-methyl-1-carboxymethyl-2-pyridinone

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

HCl gas was bubbled through a stirred suspension of 3-benzylsulfonylamino-6-methyl-1-(tert-butoxycarbonylmethyl)-2-pyridinone (1.4 g, 3.57 mmol), as prepared in the preceding step, in ethyl acetate (15 mL) at 0° C. until a solution was formed. After 2 h at room temperature, a thick suspension was formed. The mixture was degassed with nitrogen and filtered to give the title compound a white solid (1.1 g, 92%). 1H-NMR (300 MHz, CDCl3) δ8.67 (s, 1H), 7.34 (m, 5H), 7.12 (d, J=7.5 Hz, 1H), 6.10 (d, J=7.6 Hz, 1H), 4.78 (s, 2H), 4.51 (s, 2H), 2.26 (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-7c6e8221f50d479891b59648f49f98a8
Source dataset
uspto-grants-2003_05
Patent number
US06566379B1

Reaction notes

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