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

HRID 642153Notes

Reaction equation

HRID 642153 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)hydrazinecarboxylate

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 (Fluka) (750 μL) at rt. After 30 min, aminomethyl resin (Polymers Laboratories PL-AMS, 1.96 mmol/g, 970 mg) was added and the resulting mixture was stirred overnight 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 50° C. for 5 hrs. The title compound (981 mg) was obtained as a white solid (63%) in 99.8% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Workup

  1. additionaminomethyl resin (Polymers Laboratories PL-AMS, 1.96 mmol/g, 970 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 50° C. for 5 hrs

Sources & evidence

ORD record
ord-7b06b43fd7754fb4a180d08b55e64a92
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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