HCID 11242860, compound → HCID 11482841, compound

HRID 1443329Notes

Reaction equation

HRID 1443329 reaction equation
[C:1]([NH:9][NH:10][C@H:11]([C@@H:17]([CH3:20])[CH:18]=[CH2:19])[C:12]([O:14][CH2:15][CH3:16])=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].C(O)C>[C:1]([NH:9][NH:10][C@H:11]([C@@H:17]([CH3:20])[CH2:18][CH3:19])[C:12]([O:14][CH2:15][CH3:16])=[O:13])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 11242860HCID 11242860, compound

Product 1

HCID 11482841HCID 11482841, compoundYield 71.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% palladium activated carbon (20 mg) was added to an ethanol solution (5 mL) of (2R, 3S)-ethyl 2-(N′-benzoylhydrazino)-3-methyl-4-pentenoate (116 mg, 0.4 mmol), and the reaction mixture was stirred at a room temperature for 12 hours. The reaction mixture was filtered to obtain filtrate, and the palladium activated carbon was washed with ethanol (15 mL). The filtrate and the ethanol were distillated under a reduced pressure to remove the solvent, and the residue was purified and isolated by silica gel column chromatography (hexane/ethyl acetate=2/1) to obtain (2R, 3S)-ethyl 2-(N′-benzoylhydrazino)-3-methylpentanoate (80 mg, yield: 70%):

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto obtain filtrate
  3. washthe palladium activated carbon was washed with ethanol (15 mL)
  4. customto remove the solvent
  5. customthe residue was purified
  6. customisolated by silica gel column chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-fff2039a4ab84114b550590e3385e6c9
Source dataset
uspto-grants-2010_02
Patent number
US07659424B2

Reaction notes

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