Sodium Hydroxide → HCID 23696312, compound

HRID 2299204Notes

Reaction equation

HRID 2299204 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH:12]2[C:17]([C:18]([O:20]CC)=[O:19])=[CH:16][CH2:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])=[C:4]([F:23])[CH:3]=1.[OH-].[Na+:25]>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH:12]2[C:17]([C:18]([O-:20])=[O:19])=[CH:16][CH2:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])=[C:4]([F:23])[CH:3]=1.[Na+:25]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 9863761HCID 9863761, compound2×

Product 1

HCID 23696312HCID 23696312, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
55 °C

Procedure

A solution of ethyl 6-[N-(4-chloro-2-fluorophenyl)sulfamoyl]-1-cyclohexene-1-carboxylate obtained in Example 1 (Compound 1, 210 mg) in acetonitrile (29 ml) was admixed with a 1N aqueous solution of sodium hydroxide (29 ml) and the mixture was stirred at 55° C. for 12 hours. The mixture was concentrated under reduced pressure and the residue was purified by CHP-20P column chromatography (eluent: water→methanol/water=1/1). The effluent was concentrated under reduced pressure and the residue was dissolved in water (5 ml) and lyophilized to yield sodium 6-[N-(4-chloro-2-fluorophenyl)sulfamoyl]-1-cyclohexene-1-carboxylate (43 mg) as a white powder.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was purified by CHP-20P column chromatography (eluent: water→methanol/water=1/1)
  3. concentrationThe effluent was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in water (5 ml)

Sources & evidence

ORD record
ord-8df52c0bd3924fce8d64fed1061c42de
Source dataset
uspto-grants-2002_12
Patent number
US06495604B1

Reaction notes

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