2-(Carbobenzyloxy-alpha-methylalanyl]aminomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one → 5-Methyl-2-(alpha-methylalanyl)aminomethyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one
Reaction equation
C([NH:11][C:12]([CH3:33])([C:14]([NH:16][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:15])[CH3:13])(OCC1C=CC=CC=1)=O.[H][H]>CN(C)C=O.CO.[Pd]>[CH3:30][C:28]1[CH:29]=[C:20]2[CH2:19][CH:18]([CH2:17][NH:16][C:14](=[O:15])[C:12]([CH3:13])([CH3:33])[NH2:11])[O:32][C:21]2=[C:22]2[C:27]=1[NH:26][C:25](=[O:31])[CH:24]=[CH:23]2Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Procedure
2-(N-Carbobenzyloxy-α-methylalanyl]aminomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one (2.46 g, 5.48 mmol) was dissolved in dimethylformamide (190 ml). To the obtained solution, 10% palladium-on-carbon (2.46 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. The resultant residue was dissolved in methanol (70 ml). To the obtained solution, 1.37 N-HCl--methanol (4.39 ml) was added at room temperature, followed by condensing under reduced pressure. The resultant residue was submitted to a recrystallizing procedure using methanol to obtain 1.65 g of the title compound as pale yellow powdery crystals (85.6%).
Workup
- filtrationThe reaction mixture was filtered
- customcondensed
- customfollowed by condensing under reduced pressure
Sources & evidence
- ORD record
- ord-7f4003da581b48ad800ed46ea824312c
- Source dataset
- uspto-grants-1996_11
- Patent number
- US05576324
Reaction notes
Loading…