HCID 14460949, compound → HCID 67902356, compound

HRID 373398Notes

Reaction equation

HRID 373398 reaction equation
[C:1]1([C@@H:7]([N:9]2[C:13]3[CH2:14][O:15][C:16](=[O:17])[C:12]=3[NH:11][C:10]2=[O:18])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)(=O)C.[Pd]>[C:1]1([C@@H:7]([N:9]2[C@H:13]3[CH2:14][O:15][C:16](=[O:17])[C@H:12]3[NH:11][C:10]2=[O:18])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 14460949HCID 14460949, compound

Product 1

HCID 67902356HCID 67902356, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 3.7 g (15.15 mmol) of 1-[(S)-(1-phenylethyl)]-1H-furo-[3,4-d]-imidazol-2,4(3H,6H)-dione in 100 ml of acetic acid is placed in a 250-ml autoclave and 0.4 g of palladium on activated carbon (5 percent) was added. Then the autoclave was flushed twice successively with hydrogen and filled to 50 bars. This mixture was stirred for 15 hours at room temperature. The catalyst was then filtered off. The solvent was evaporated at 20 mbars and the residue was chromatographed over silica gel with ethyl acetate. 2.0 g (54 percent yield) of the title product was eluted. Recrystallization in methanol yields white needles. Concerning the product: Melting point: 123°-125° C.

Workup

  1. additionwas added
  2. customThen the autoclave was flushed twice successively with hydrogen
  3. additionfilled to 50 bars
  4. filtrationThe catalyst was then filtered off
  5. customThe solvent was evaporated at 20 mbars
  6. customthe residue was chromatographed over silica gel with ethyl acetate

Sources & evidence

ORD record
ord-b34c04659d2940449ae82a1f9d47e794
Source dataset
uspto-grants-1992_11
Patent number
US05162540

Reaction notes

Loading…