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

HRID 642171

反応式

HRID 642171 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 3283Diethyl Ether溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ef6973d6faaa43b9a5fa8f786960a0d4
出典データセット
uspto-grants-2010_04
特許番号
US07696231B2

関連ノート

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