DL-Tyrosine → 6-Bromo-2-[1-carboxy-2-(4-hydroxy-phenyl)-ethylamino]-quinoline-3-carboxylic acid

HRID 2065671Notes

Reaction equation

HRID 2065671 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7](Cl)[C:6]([C:13]([OH:15])=[O:14])=[CH:5]2.[NH2:16][CH:17]([C:26]([OH:28])=[O:27])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH:16][CH:17]([C:26]([OH:28])=[O:27])[CH2:18][C:19]1[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=1)[C:6]([C:13]([OH:15])=[O:14])=[CH:5]2

Participants

4

Reactant 2

HCID 1153DL-TyrosineHCID 242660726-Bromo-2-chloroquinoline-3-carboxylic acid

Product 1

HCID 452565296-Bromo-2-[1-carboxy-2-(4-hydroxy-phenyl)-ethylamino]-quinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In close analogy to the procedure described in Example 1, 6-bromo-2-chloroquinoline-3-carboxylic acid is reacted with DL-tyrosine in DMSO to provide the title compound in good yield.

Sources & evidence

ORD record
ord-3800546910bc4129874f9e98cd4d3cb7
Source dataset
uspto-grants-2012_10
Patent number
US08288549B2

Reaction notes

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