L-Tyrosine → 2-[(S)-1-Carboxy-2-(4-hydroxy-phenyl)-ethylamino]-6,8-dichloro-quinoline-3-carboxylic acid

HRID 2065688Notes

Reaction equation

HRID 2065688 reaction equation
Cl[C:2]1[C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]2[C:4](=[C:5]([Cl:16])[CH:6]=[C:7]([Cl:15])[CH:8]=2)[N:3]=1.[NH2:17][C@H:18]([C:27]([OH:29])=[O:28])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1>O>[C:27]([C@@H:18]([NH:17][C:2]1[C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]2[C:4](=[C:5]([Cl:16])[CH:6]=[C:7]([Cl:15])[CH:8]=2)[N:3]=1)[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)([OH:29])=[O:28]

Participants

4

Reactant 2

HCID 6057L-TyrosineHCID 866563792,6,8-Trichloroquinoline-3-carboxylic acid

Product 1

HCID 673601542-[(S)-1-Carboxy-2-(4-hydroxy-phenyl)-ethylamino]-6,8-dichloro-quinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In close analogy to the procedure described in Example 1, 2,6,8-trichloroquinoline-3-carboxylic acid is reacted with L-tyrosine in H2O to provide the title compound in good yield.

Sources & evidence

ORD record
ord-5fb6a4a51f584765b33e41ce73e422d3
Source dataset
uspto-grants-2012_10
Patent number
US08288549B2

Reaction notes

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