HCID 9858173, compound → HCID 9879038, compound

HRID 1744026Notes

Reaction equation

HRID 1744026 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][CH2:15][CH2:16][C:17]([CH3:22])([N+:19]([O-])=O)[CH3:18])[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.O.[C].[Pd]>[CH3:13][O:12][C:10](=[O:11])[C@H:9]([CH2:14][CH2:15][CH2:16][C:17]([CH3:22])([CH3:18])[NH2:19])[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7]

Participants

6

Reactant 2

HCID 9858173HCID 9858173, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9879038HCID 9879038, compoundYield 77.3%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl (S)-2-t-butoxycarbonylamino-6-methyl-6-nitroheptanoate (500 mg, 1.57 mmol) was dissolved in methanol (8 ml) and water (0.5 ml), and 5% palladium-carbon (219 mg, 50% wet) and ferrous sulfate 7 hydrate (1.32 g, 4.75 mmol) were added. The mixture was stirred at a hydrogen pressure of 3 atm and room temperature for 3 h. Palladium-carbon was removed by filtration and methanol was evaporated by concentration under reduced pressure. Ethyl acetate (50 ml), water (50 ml) and sodium carbonate were added for pH adjustment to 10 and extraction. After layer partitioning, the aqueous layer was extracted again with toluene-isopropyl alcohol (1:1, 100 ml). The organic layers were combined and the solvent was evaporated by concentration under reduced pressure to give the objective compound (350 mg, yield 77.3%).

Workup

  1. customPalladium-carbon was removed by filtration and methanol
  2. customwas evaporated by concentration under reduced pressure
  3. additionEthyl acetate (50 ml), water (50 ml) and sodium carbonate were added for pH adjustment to 10 and extraction
  4. customAfter layer partitioning
  5. extractionthe aqueous layer was extracted again with toluene-isopropyl alcohol (1:1, 100 ml)
  6. customthe solvent was evaporated by concentration under reduced pressure

Sources & evidence

ORD record
ord-ed889571de78456bb83f863d3edc989b
Source dataset
uspto-grants-2006_03
Patent number
US07012152B2

Reaction notes

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