Dimethylformamide → 2-(D-Alanylmethyl)-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one

HRID 1900772Notes

Reaction equation

HRID 1900772 reaction equation
C(NCCC(N[CH2:17][CH:18]1[O:32][C:21]2=[C:22]3[C:27](=[C:28]([CH3:30])[CH:29]=[C:20]2[CH2:19]1)[NH:26][C:25](=[O:31])[CH:24]=[CH:23]3)=O)(OCC1C=CC=CC=1)=O.[H][H].[CH3:35]O.C[CH2:38][O:39]CC.C[N:43]([CH3:46])C=O>CO.[Pd]>[NH2:43][C@@H:46]([C:38]([CH2:17][CH:18]1[O:32][C:21]2=[C:22]3[C:27](=[C:28]([CH3:30])[CH:29]=[C:20]2[CH2:19]1)[NH:26][C:25](=[O:31])[CH:24]=[CH:23]3)=[O:39])[CH3:35]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 21864698Diethyl ether methanolHCID 678009322-(Carbobenzyloxy-beta-alanyl]aminomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 228670612-(D-Alanylmethyl)-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-oneYield 88.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-(Carbobenzyloxy-β-alanyl]aminomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one (2.61 g, 6.00 mmol) was dissolved in dimethylformamide (200 ml). To the obtained solution, 10% palladium-on-carbon (2.61 g) was added, followed by stirring at room temperature for 5 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 (50 ml). To the obtained solution, 1.37 N-HCl--methanol (4.82 ml) was added at room temperature, followed by being submitted to a recrystallizing procedure using methanol ether to obtain 1.80 g of the title compound as pale yellow powdery crystals (88.8%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-024c217bf1f7489b8a443e7808699a76
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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