Sodium Hydroxide → 592542-60-4

HRID 424358Notes

Reaction equation

HRID 424358 reaction equation
[CH3:1][O:2][C:3]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[C:24]([O:30][CH3:31])[C:4]=1/[CH:5]=[CH:6]/[S:7]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:22][CH3:23])=[C:15]([NH:17][CH2:18][C:19]([OH:21])=[O:20])[CH:16]=1)(=[O:9])=[O:8].[OH-].[Na+:33]>C(O)C>[Na+:33].[CH3:1][O:2][C:3]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[C:24]([O:30][CH3:31])[C:4]=1/[CH:5]=[CH:6]/[S:7]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:22][CH3:23])=[C:15]([NH:17][CH2:18][C:19]([O-:21])=[O:20])[CH:16]=1)(=[O:8])=[O:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 6918736Rigosertib

Product 1

HCID 23696523592542-60-4Yield 85.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(E)-2-(5-((2,4,6-Trimethoxystyrylsulfonyl)methyl)-2-methoxyphenylamino)acetic acid (15 g, 0.032 mol) is dissolved in ethanol (150 ml) and 1 N NaOH (1.28 g in 33 ml of water, 0.032 mol) is added, adjusted pH to 7.5-8.0 and stirred at room temperature for 1 h. The reaction is cooled to 0° C., and the precipitated solid is collected by filtration, washed with cold ethanol, and finally with hexane and dried under vacuum to give (E)-2-(5-((2,4,6-trimethoxystyrylsulfonyl)methyl)-2-methoxyphenylamino)acetic acid sodium salt (13 g, 84%).

Workup

  1. temperatureThe reaction is cooled to 0° C.
  2. filtrationthe precipitated solid is collected by filtration
  3. washwashed with cold ethanol
  4. dry with materialfinally with hexane and dried under vacuum

Sources & evidence

ORD record
ord-2ad85619fcf3422bb3fb6bc6e2cbd652
Source dataset
uspto-grants-2012_01
Patent number
US08106033B2

Reaction notes

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