L-Tyrosine, N-(1,1-dimethylethoxy)carbonyl- → 2-{(S)-1-Carboxy-2-[4-(3-carboxy-6,8-dichloro-quinolin-2-yloxy)-phenyl]-ethylamino}-6,8-dichloro-quinoline-3-carboxylic acid

HRID 2065692Notes

Reaction equation

HRID 2065692 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.[C:17]([NH:24][C@H:25]([C:34]([OH:36])=[O:35])[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=1)(OC(C)(C)C)=O>O>[C:34]([C@@H:25]([NH:24][C:17]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)[CH2:26][C:27]1[CH:28]=[CH:29][C:30]([O:33][C:2]2[C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]3[C:4](=[C:5]([Cl:16])[CH:6]=[C:7]([Cl:15])[CH:8]=3)[N:3]=2)=[CH:31][CH:32]=1)([OH:36])=[O:35]

Participants

4

Reactant 2

HCID 117439L-Tyrosine, N-(1,1-dimethylethoxy)carbonyl-HCID 866563792,6,8-Trichloroquinoline-3-carboxylic acid

Product 1

HCID 673578832-{(S)-1-Carboxy-2-[4-(3-carboxy-6,8-dichloro-quinolin-2-yloxy)-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 N-Boc-L-tyrosine in H2O to provide the title compound in good yield.

Sources & evidence

ORD record
ord-24f0e85b5efc41f281c5cdb34bfdcded
Source dataset
uspto-grants-2012_10
Patent number
US08288549B2

Reaction notes

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