Sodium Hydroxide → (E)-2-(5-((2,4,6-trimethoxystyrylsulfonyl)methyl)-2-methoxyphenylamino)propanoic acid

HRID 1183218Notes

Reaction equation

HRID 1183218 reaction equation
[CH3:1][O:2][C:3]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[C:26]([O:32][CH3:33])[C:4]=1/[CH:5]=[CH:6]/[S:7]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:24][CH3:25])=[C:15]([NH:17][CH:18]([CH3:23])[C:19]([O:21]C)=[O:20])[CH:16]=1)(=[O:9])=[O:8].[OH-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[C:26]([O:32][CH3:33])[C:4]=1/[CH:5]=[CH:6]/[S:7]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:24][CH3:25])=[C:15]([NH:17][CH:18]([CH3:23])[C:19]([OH:21])=[O:20])[CH:16]=1)(=[O:8])=[O:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54579438methyl(E)-2-(5-((2,4,6-trimethoxystyrylsulfonyl)methyl)-2-methoxyphenylamino)propanoate

Product 1

HCID 10389765(E)-2-(5-((2,4,6-trimethoxystyrylsulfonyl)methyl)-2-methoxyphenylamino)propanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl (E)-2-(5-((2,4,6-trimethoxystyrylsulfonyl)methyl)-2-methoxyphenylamino)propanoate (0.1 mol) in ethanol (200 mL), was added sodium hydroxide (20% aqueous solution, 200 mL). The resulting mixture was heated at reflux for 2.5 h. The reaction was monitored by TLC. When the reaction was complete, the volatiles were removed under vacuum and the resulting residue was acidified to pH 4 by addition of acetic acid. A solid precipitate formed. The precipitate was separated by filtration. The filtered solid was recrystallized twice from acetone to provide the desired (E)-2-(5-((2,4,6-trimethoxystyrylsulfonyl)methyl)-2-methoxyphenylamino)propanoic acid. m.p. 176-180° C.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 2.5 h
  3. customthe volatiles were removed under vacuum
  4. additionthe resulting residue was acidified to pH 4 by addition of acetic acid
  5. customA solid precipitate formed
  6. customThe precipitate was separated by filtration
  7. customThe filtered solid was recrystallized twice from acetone

Sources & evidence

ORD record
ord-081bb333fd63418e8a3f2b79d84197b5
Source dataset
uspto-grants-2014_03
Patent number
US08664272B2

Reaction notes

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