Methyl 4-(chlorocarbonyl)benzoate → Tert-butyl 2-(4-{[4-(methoxycarbonyl)benzoyl]amino}benzoyl)hydrazinecarboxylate

HRID 642155노트

반응식

HRID 642155 반응식
[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[C:20]([C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=1)=[O:21]>N1C=CC=CC=1>[CH3:29][O:28][C:26]([C:25]1[CH:30]=[CH:31][C:22]([C: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])=[CH:23][CH:24]=1)=[O:27]

참가 물질

4

반응물 2

HCID 81850Methyl 4-(chlorocarbonyl)benzoateHCID 68409588Tert-butyl 2-(4-aminobenzoyl)hydrazinecarboxylate

생성물 1

HCID 10179961Tert-butyl 2-(4-{[4-(methoxycarbonyl)benzoyl]amino}benzoyl)hydrazinecarboxylate수율 85.7%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a solution of tert-butyl 2-(4-aminobenzoyl)hydrazinecarboxylate (1.0 g, 3.98 mmol) in anhydrous pyridine (20 mL) was added dropwise methyl 4-(chlorocarbonyl)benzoate (TCI) (948 mg, 4.78 mmol) at rt. After 50 min, aminomethyl resin (Polymers Laboratories PL-AMS, 1.96 mmol/g, 960 mg) was added and the resulting mixture was stirred for 22 hrs at rt After filtration and rinsing the resin, water (160 mL) was added into the filtrate and a white solid precipitated out. Filtration and washing with water gave a white solid, which was dried under vacuo at 60° C. for 15 hrs. The title compound (1.41 g) was obtained as a white solid (85%) in 98.7% purity by HPLC (MaxPlot detection between 230 and 400 mn).

후처리

  1. additionaminomethyl resin (Polymers Laboratories PL-AMS, 1.96 mmol/g, 960 mg) was added
  2. filtrationAfter filtration
  3. washrinsing the resin, water (160 mL)
  4. additionwas added into the filtrate
  5. customa white solid precipitated out
  6. filtrationFiltration
  7. washwashing with water
  8. customgave a white solid, which
  9. customwas dried under vacuo at 60° C. for 15 hrs

출처 및 근거

ORD 기록
ord-8634b40b7cba4577bce3e6c9ecee8837
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696231B2

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