Hydrochloric Acid → (E)-2-(2-methoxy-5-((2,4,6-trimethoxystyrylsulfonyl)methyl)pyridin-3-ylamino)acetic acid

HRID 72654Notes

Reaction equation

HRID 72654 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[C:10]([NH:11][CH2:12][C:13]([O:15]CC)=[O:14])=[CH:9][C:8]([CH2:18][S:19](/[CH:22]=[CH:23]/[C:24]2[C:29]([O:30][CH3:31])=[CH:28][C:27]([O:32][CH3:33])=[CH:26][C:25]=2[O:34][CH3:35])(=[O:21])=[O:20])=[CH:7][N:6]=1.Cl>O>[CH3:3][O:4][C:5]1[C:10]([NH:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:9][C:8]([CH2:18][S:19](/[CH:22]=[CH:23]/[C:24]2[C:29]([O:30][CH3:31])=[CH:28][C:27]([O:32][CH3:33])=[CH:26][C:25]=2[O:34][CH3:35])(=[O:21])=[O:20])=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 56598518HCID 56598518, compound

Product 1

HCID 86690904(E)-2-(2-methoxy-5-((2,4,6-trimethoxystyrylsulfonyl)methyl)pyridin-3-ylamino)acetic acidYield 133.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydroxide (4 mg, ° Animal) was added to a solution of (E)-ethyl 2-(2-methoxy-5-((2,4,6-trim ethoxystyrylsulfonyl)methyl)pyridin-3-ylamino)acetate (19 mg, 0.04 mmol) in H2O (10 mL). The mixture was stirred at room temperature for 1 h. The residue was acidified by addition of 2M aq HCl and extracted with EtOAc (3×10 mL). The combined extracts was washed with brine, dried on MgSO4, and filtered. The residue was further purified by silica gel chromatography, eluting with PE/EtOAc (2:3, v/v) to afford pure product as a white solid (24.2 mg, 70%). 1H-NMR (CDCl3): δ 3.82 (s, 6H, 2×OCH3), 3.83 (s, 3H, OCH3), 3.85 (d, 2H, J=1.6 Hz, CH2), 3.90 (s, 2H, CH2), 3.96 (s, 3H, OCH3), 6.08 (s, 2H, Ph-H), 6.72 (s, 1H, Py-H), 7.02 (d, 1H, J=15.6 Hz, CH), 7.43 (s, 1H, Py-H), 7.78 (d, 1H, J=15.6 Hz, CH); HR-MS (ESI+) m/z: 451.1245 [M−H]−, C20H24N2O8S requires 452.1253.

Workup

  1. extractionextracted with EtOAc (3×10 mL)
  2. washThe combined extracts was washed with brine
  3. customdried on MgSO4
  4. filtrationfiltered
  5. customThe residue was further purified by silica gel chromatography
  6. washeluting with PE/EtOAc (2:3

Sources & evidence

ORD record
ord-d274d1b3c5ec4761a49e6bdbc06e0a8c
Source dataset
uspto-grants-2014_09
Patent number
US08829003B2

Reaction notes

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