Methane → HCID 57157549, compound

HRID 2225906Notes

Reaction equation

HRID 2225906 reaction equation
[NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:2]([C:7]([CH:9](C(OCC1C=CC=CC=1)=O)[F:10])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].C>C(O)C.[Pd]>[NH:1]([C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])[C@H:2]([C:7]([CH2:9][F:10])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5]

Participants

5

Reactant 2

HCID 297MethaneHCID 15228940HCID 15228940, compound

Product 1

HCID 57157549HCID 57157549, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of Boc-LeuCHFCOOBzl (3.58 g, 9.39 mmol) in ethanol (50 mL) was added 10% palladium on active charcoal (0.36 g). The mixture was subjected to hydrogenolysis on a Parr shaker for 36 hours. The solution was filtered and the solvent was evaporated. The residue was dissolved in ethyl acetate (100 mL), washed with saturated aqueous NaHCO3 (50 mL), brine (50 mL), dried over MgSO4, filtered, and evaporated to give an almost colorless, viscous oil, Boc-LeuCH2F (1.53 g, 66%).

Workup

  1. filtrationThe solution was filtered
  2. customthe solvent was evaporated
  3. dissolutionThe residue was dissolved in ethyl acetate (100 mL)
  4. washwashed with saturated aqueous NaHCO3 (50 mL), brine (50 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-3bb49e5541f94fc1a3e4fa20b296e1cf
Source dataset
uspto-grants-1994_09
Patent number
US05344939

Reaction notes

Loading…