Sodium Hydroxide → 4-(5-(Aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoyloxy)butanoic acid

HRID 2357729Notes

Reaction equation

HRID 2357729 reaction equation
[NH2:1][S:2]([C:5]1[C:6]([Cl:29])=[CH:7][C:8]([NH:22][CH2:23][C:24]2[O:25][CH:26]=[CH:27][CH:28]=2)=[C:9]([CH:21]=1)[C:10]([O:12][CH2:13][CH2:14][CH2:15][C:16]([O:18]CC)=[O:17])=[O:11])(=[O:4])=[O:3].[OH-].[Na+]>C(O)C>[NH2:1][S:2]([C:5]1[C:6]([Cl:29])=[CH:7][C:8]([NH:22][CH2:23][C:24]2[O:25][CH:26]=[CH:27][CH:28]=2)=[C:9]([CH:21]=1)[C:10]([O:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[O:11])(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68456450HCID 68456450, compound

Product 1

HCID 593891294-(5-(Aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoyloxy)butanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 4-(5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoyloxy)butanoate (300) (0.060 mole) in ethanol (100 mL) is cooled in an ice water bath. A solution of 1.0 N sodium hydroxide (60 mL) is added dropwise with stirring, and the reaction is stirred for 12 hours at ambient temperature. The volatiles is removed by spin evaporation in vacuo. The residue is dissolved in cold water, and the solution is washed with diethyl ether. The aqueous solution is cooled in an ice bath and acidified by dropwise addition of 1.0 N hydrochloric acid solution (60 mL). The resulting solid may be collected and recrystallized to give 4-(5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoyloxy)butanoic acid.

Workup

  1. temperatureis cooled in an ice water bath
  2. stirringthe reaction is stirred for 12 hours at ambient temperature
  3. customThe volatiles is removed by spin evaporation in vacuo
  4. dissolutionThe residue is dissolved in cold water
  5. washthe solution is washed with diethyl ether
  6. temperatureThe aqueous solution is cooled in an ice bath
  7. additionacidified by dropwise addition of 1.0 N hydrochloric acid solution (60 mL)
  8. customThe resulting solid may be collected
  9. customrecrystallized

Sources & evidence

ORD record
ord-ed2d6777587c45caa921e28072438baa
Source dataset
uspto-grants-2010_07
Patent number
US07763612B2

Reaction notes

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