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

HRID 48883Notes

Reaction equation

HRID 48883 reaction equation
Cl.[CH2:2]([S:9]([NH:12][C:13]1[C:14](=[O:27])[N:15]([CH2:19][C:20]([O:22]C(C)(C)C)=[O:21])[CH:16]=[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:27])[N:15]([CH2:19][C:20]([OH:22])=[O:21])[CH:16]=[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 120720253-Benzylsulfonylamino-1-(tert-butoxycarbonylmethyl)-2-pyridinone

Product 1

HCID 158866933-Benzylsulfonylamino-1-carboxymethyl-2-pyridinone

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

HCl gas was bubbled through a stirred suspension of 3-benzylsulfonylamino-1-(tert-butoxycarbonylmethyl)-2-pyridinone (1.7 g, 4.5 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 (1.4 g, 97%). 1H-NMR (300 MHz, CDCl3) δ8.76 (s, 1H), 7.45 (dd, J=7.0, 1.8 Hz, 1H), 7.32 (m, 5H), 7.19 (dd, J=7.2, 1.8 Hz, 1H), 6.16 (t, J=7.1 Hz, 1H), 4.69 (s, 2H), 4.56 (s, 2H).

Workup

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

Sources & evidence

ORD record
ord-08d8481a22a5496481588a5157b4af6b
Source dataset
uspto-grants-2004_03
Patent number
US06706021B2

Reaction notes

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