HCID 53681954, compound → HCID 53793415, compound

HRID 726639Notes

Reaction equation

HRID 726639 reaction equation
[CH3:1][O:2][C:3](=[O:40])[C:4]([NH:29]C(OCC1C=CC=CC=1)=O)=[CH:5][C:6]1[C:15]([CH2:16][P:17]([O:22][CH2:23][CH3:24])([O:19][CH2:20][CH3:21])=[O:18])=[CH:14][C:13]2[C:8](=[CH:9][C:10]([O:27][CH3:28])=[C:11]([O:25][CH3:26])[CH:12]=2)[N:7]=1>[Pd].CO>[CH3:1][O:2][C:3](=[O:40])[CH:4]([NH2:29])[CH2:5][C:6]1[C:15]([CH2:16][P:17]([O:19][CH2:20][CH3:21])([O:22][CH2:23][CH3:24])=[O:18])=[CH:14][C:13]2[C:8](=[CH:9][C:10]([O:27][CH3:28])=[C:11]([O:25][CH3:26])[CH:12]=2)[N:7]=1

Participants

4

Reactant 1

HCID 53681954HCID 53681954, compound

Product 1

HCID 53793415HCID 53793415, compoundYield 81.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of α-(benzyloxycarbonylamino)-3-(diethylphosphonomethyl)-6,7-dimethoxy-2-quinolineacrylic acid methyl ester (0.14 g, 0.25 mmol) and a catalytic amount of palladium on charcoal (10%) in MeOH (10 ml) was hydrogenated at 4 bar for 20 h. Filtration and chromatographic purification gave 0.09 g α-amino-3-(diethylphosphonomethyl)-6,7-dimethoxy-2-quinolinepropanoic acid methyl ester.

Workup

  1. filtrationFiltration and chromatographic purification

Sources & evidence

ORD record
ord-125e601c34bd41b4b53d1cb78c903d15
Source dataset
uspto-grants-1998_01
Patent number
US05710139

Reaction notes

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