Butanoic acid, 4-chloro-4-oxo-, methyl ester → Tert-butyl 2-{4-[(4-methoxy-4-oxobutanoyl)amino]benzoyl}hydrazinecarboxylate

HRID 642149Notes

Reaction equation

HRID 642149 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.[C:19]([CH2:23][CH2:24][C:25](Cl)=[O:26])([O:21][CH3:22])=[O:20]>N1C=CC=CC=1>[CH3:22][O:21][C:19](=[O:20])[CH2:23][CH2:24][C:25]([NH:1][C:2]1[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]=1)=[O:26]

Participants

4

Reactant 2

HCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl esterHCID 68409588Tert-butyl 2-(4-aminobenzoyl)hydrazinecarboxylate

Product 1

HCID 9925313Tert-butyl 2-{4-[(4-methoxy-4-oxobutanoyl)amino]benzoyl}hydrazinecarboxylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of tert-butyl 2-(4-aminobenzoyl)hydrazinecarboxylate (500 mg, 1.99 mmol) in anhydrous pyridine (10 mL) was added dropwise 3-carbomethoxypropionyl chloride (Fluka) (300 μL) at rt. After 60 min, aminomethyl resin (Polymers Laboratories PL-AMS, 1.96 mmol/g, 400 mg) was added and the resulting mixture was stirred overnight at rt. After filtration and rinsing the resin, water (80 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 70° C. for 2 hrs. The title compound (461 mg) was obtained as a white solid (63%) in 96.0% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Workup

  1. additionaminomethyl resin (Polymers Laboratories PL-AMS, 1.96 mmol/g, 400 mg) was added
  2. filtrationAfter filtration
  3. washrinsing the resin, water (80 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 70° C. for 2 hrs

Sources & evidence

ORD record
ord-b481784419224eb9b514127c1d210082
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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