Diethyl Ether → HCID 57022354, compound

HRID 1900776Notes

Reaction equation

HRID 1900776 reaction equation
C([CH:11]([C:13]([NH:15][CH2:16][CH:17]1[O:31][C:20]2=[C:21]3[C:26](=[C:27]([CH3:29])[CH:28]=[C:19]2[CH2:18]1)[NH:25][C:24](=[O:30])[CH:23]=[CH:22]3)=[O:14])[NH2:12])(OCC1C=CC=CC=1)=O.[H][H].CCOCC>CN(C)C=O.CO.Cl.O1CCOCC1.[Pd]>[NH2:12][CH2:11][C:13]([NH:15][CH2:16][CH:17]1[O:31][C:20]2=[C:21]3[C:26](=[C:27]([CH3:29])[CH:28]=[C:19]2[CH2:18]1)[NH:25][C:24](=[O:30])[CH:23]=[CH:22]3)=[O:14]

Participants

8

Reactant 3

HCID 3283Diethyl EtherHCID 67771068HCID 67771068, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57022354HCID 57022354, compoundYield 106.2%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 6228DimethylformamideSolventHCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

2-Carbobenzyloxyglycylaminomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one (2.00 g, 4.75 mmol) was dissolved in dimethylformamide (250 ml). To the obtained solution, 10% palladium-on-carbon (2.00 g) was added, followed by stirring at room temperature for 3 hours in the atmosphere of hydrogen. The reaction mixture was filtered, and the filtrate was condensed under reduced pressure. The resultant residue was dissolved in methanol (20 ml), to which 4N-HCl/dioxane (1.2 ml) was added, and the mixture was condensed under reduced pressure at room temperature. The resultant residue was submitted to a recrystallizing procedure using methanol--ether to obtain 1.45 g of the title compound as pale yellow powdery crystals (94.6%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customcondensed under reduced pressure
  3. additionwas added
  4. customcondensed under reduced pressure at room temperature

Sources & evidence

ORD record
ord-d59d7c40e6aa430f8bb1e3ed209fa895
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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