Methyl 6-chloro-6-oxohexanoate → Tert-butyl 2-{4-[(6-methoxy-6-oxohexanoyl)amino]benzoyl)hydrazinecarboxylate

HRID 642157Notes

Reaction equation

HRID 642157 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](=[O:29])[CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26]>N1C=CC=CC=1>[CH3:28][O:27][C:25](=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21][C:20]([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:29]

Participants

4

Reactant 2

HCID 520737Methyl 6-chloro-6-oxohexanoateHCID 68409588Tert-butyl 2-(4-aminobenzoyl)hydrazinecarboxylate

Product 1

HCID 10293973Tert-butyl 2-{4-[(6-methoxy-6-oxohexanoyl)amino]benzoyl)hydrazinecarboxylateYield 81.1%

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 6-chloro-6-oxohexanoate (Aldrich) (660 μL, 4.78 mmol) at rt. After 90 min, aminomethyl resin (Polymers Laboratories PL-AMS, 1.96 mmol/g, 960 mg) was added and the resulting mixture was stirred for 20 hrs at rt. After filtration and rinsing the resin, water (200 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 3 hrs. The title compound (1.27 g) was obtained as a white solid (80%) in 95.1% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Workup

  1. additionaminomethyl resin (Polymers Laboratories PL-AMS, 1.96 mmol/g, 960 mg) was added
  2. filtrationAfter filtration
  3. washrinsing the resin, water (200 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 3 hrs

Sources & evidence

ORD record
ord-8839e22539404353a236df2dfff90be5
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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