Hydrochloric Acid → HCID 24883170, compound

HRID 1009489Notes

Reaction equation

HRID 1009489 reaction equation
[Cl:1][C:2]1[C:3]([CH3:34])=[C:4]([N:8]([S:24]([C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=2)(=[O:26])=[O:25])[CH2:9][C:10]([NH:12][CH2:13][C:14]2[CH:23]=[CH:22][C:17]([C:18]([O:20]C)=[O:19])=[CH:16][CH:15]=2)=[O:11])[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].Cl>CO.C1COCC1>[Cl:1][C:2]1[C:3]([CH3:34])=[C:4]([N:8]([S:24]([C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=2)(=[O:25])=[O:26])[CH2:9][C:10]([NH:12][CH2:13][C:14]2[CH:23]=[CH:22][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=2)=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58009494HCID 58009494, compound

Product 1

HCID 24883170HCID 24883170, compoundYield 200.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

308 mg of methyl 4-[({N-(3-chloro-2-methylphenyl)-N-[(4-methylphenyl)sulfonyl]glycyl}amino)methyl]benzoate was dissolved in 5.00 mL of methanol and 2.00 mL of THF, and 2.40 mL of a 1 M aqueous sodium hydroxide solution was added thereto, followed by stirring at room temperature overnight. Then, to the reaction liquid was added 3.00 mL of THF, followed by stirring at 60° C. for 4 hours. The reaction liquid was ice-cooled, acidified by addition of 2.60 mL of 1 M hydrochloric acid, and then extracted with a mixed solvent of chloroform/methanol (5/1), and the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 90:10) to obtain 601 mg of 4-[({N-(3-chloro-2-methylphenyl)-N-[(4-methylphenyl)sulfonyl]glycyl}amino)methyl]benzoic acid.

Workup

  1. customThen, to the reaction liquid
  2. stirringby stirring at 60° C. for 4 hours
  3. customThe reaction liquid
  4. temperaturecooled
  5. extractionextracted with a mixed solvent of chloroform/methanol (5/1)
  6. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe obtained residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 90:10)

Sources & evidence

ORD record
ord-b2cbeffadd214281a990ca4167116698
Source dataset
uspto-grants-2011_07
Patent number
US07973078B2

Reaction notes

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