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

HRID 2065644Notes

Reaction equation

HRID 2065644 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.[OH:17][C:18]1[CH:19]=[C:20]([CH:27]=[CH:28][CH:29]=1)[CH2:21][CH:22]([C:24]([OH:26])=[O:25])[NH2:23]>>[C:24]([CH:22]([NH:23][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)[CH2:21][C:20]1[CH:27]=[CH:28][CH:29]=[C:18]([OH:17])[CH:19]=1)([OH:26])=[O:25]

Participants

3

Reactant 2

HCID 130523-Tyrosine, DL-HCID 866563792,6,8-Trichloroquinoline-3-carboxylic acid

Product 1

HCID 452555832-[1-Carboxy-2-(3-hydroxy-phenyl)-ethylamino]-6,8-dichloro-quinoline-3-carboxylic acid

Procedure

In close analogy to the procedure described in Example 1, 2,6,8-trichloroquinoline-3-carboxylic acid is reacted with 3-hydroxy-DL-phenylalanine to provide the title compound in moderate yield. LCMS m/z 421 (M+1).

Sources & evidence

ORD record
ord-25b4d7792a9b4a498c1f83716b1054c5
Source dataset
uspto-grants-2012_10
Patent number
US08288549B2

Reaction notes

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