Diethyl Ether → HCID 22867067, compound

HRID 1900775Notes

Reaction equation

HRID 1900775 reaction equation
C([N:11]1[CH2:34][CH2:33][CH2:32][C@H:12]1[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])(OCC1C=CC=CC=1)=O.[H][H].CCOCC>CN(C)C=O.CO.[Pd]>[CH3:29][C:27]1[CH:28]=[C:19]2[CH2:18][CH:17]([CH2:16][NH:15][C:13](=[O:14])[C@@H:12]3[CH2:32][CH2:33][CH2:34][NH:11]3)[O:31][C:20]2=[C:21]2[C:26]=1[NH:25][C:24](=[O:30])[CH:23]=[CH:22]2

Participants

7

Reactant 3

HCID 3283Diethyl EtherHCID 22867055HCID 22867055, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22867067HCID 22867067, compoundYield 109.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 6228DimethylformamideSolvent

Procedure

2-(Carbobenzyloxy-L-prolyl)aminomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one (1.04 g, 2.25 mmol) was dissolved in dimethylformamide (130 ml). To the obtained solution, 10% palladium-on-carbon (1.04 g) was added, followed by stirring at room temperature for 4 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 (65 ml), to which 1.37 N-HCl--methanol (1.81 ml) was added. The mixture was condensed under reduced pressure. The resultant residue was submitted to a recrystallizing procedure using methanol--ether to obtain 807 mg of the title compound as pale yellow powdery crystals (98.6%).

Workup

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

Sources & evidence

ORD record
ord-b62858bc0b574b9fa99ae33d3fe89e96
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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