Methyl 3-[4-(chlorosulfonyl)phenyl]propanoate → Tert-butyl 2-[4-({[4-(3-methoxy-3-oxopropyl)phenyl]sulfonyl}amino)benzoyl]hydrazinecarboxylate

HRID 642171

Reaction equation

HRID 642171 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:7])=[CH:4][CH:3]=1.Cl[S:20]([C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:25][CH:24]=1)(=[O:22])=[O:21]>N1C=CC=CC=1.CCOCC>[CH3:34][O:33][C:31](=[O:32])[CH2:30][CH2:29][C:26]1[CH:27]=[CH:28][C:23]([S:20]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([NH:8][NH:9][C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])=[O:7])=[CH:17][CH:18]=2)(=[O:21])=[O:22])=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 23158517Methyl 3-[4-(chlorosulfonyl)phenyl]propanoateHCID 68409588Tert-butyl 2-(4-aminobenzoyl)hydrazinecarboxylate

Product 1

HCID 10299301Tert-butyl 2-[4-({[4-(3-methoxy-3-oxopropyl)phenyl]sulfonyl}amino)benzoyl]hydrazinecarboxylateYield 56%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of tert-butyl 2-(4-aminobenzoyl)hydrazinecarboxylate (200 mg, 0.80 mmol) in anhydrous pyridine (4 mL) was added dropwise methyl 3-(4-chlorosulfonylphenyl)propionate (251 mg, 0.96 mmol) at rt. After 60 min, aminomethyl resin (Polymers Laboratories PL-AMS, 1.96 mmol/g, 200 mg) was added and the resulting mixture was stirred for 1 hr at rt. After filtration and rinsing the resin, water (100 mL) was added into the filtrate. Extraction with EtOAc (100 mL), washing with HCl (1N, 60 mL) and an aqueous saturated solution of NaHCO3 (50 mL), drying over MgSO4 and evaporation under vacuo gave a yellow oil. The residue was taken up in Et2O and a white solid precipitated out. Filtration and washing with Et2O gave the title compound (214 mg) was obtained as a white solid (56%) in 99.3% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Workup

  1. additionaminomethyl resin (Polymers Laboratories PL-AMS, 1.96 mmol/g, 200 mg) was added
  2. filtrationAfter filtration
  3. washrinsing the resin, water (100 mL)
  4. additionwas added into the filtrate
  5. extractionExtraction with EtOAc (100 mL)
  6. washwashing with HCl (1N, 60 mL)
  7. dry with materialan aqueous saturated solution of NaHCO3 (50 mL), drying over MgSO4 and evaporation under vacuo
  8. customgave a yellow oil
  9. customa white solid precipitated out
  10. filtrationFiltration
  11. washwashing with Et2O

Sources & evidence

ORD record
ord-ef6973d6faaa43b9a5fa8f786960a0d4
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Linked notes

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