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

HRID 642155Notes

Reaction equation

HRID 642155 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[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-8634b40b7cba4577bce3e6c9ecee8837
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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