L-Phenylalanine → 2-((S)-1-Carboxy-2-phenyl-ethylamino)-6,8-dichloro-quinoline-3-carboxylic acid

HRID 2065626Notes

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:26]([OH:28])=[O:27])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[C:26]([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][CH:23]=[CH:22][CH:21]=1)([OH:28])=[O:27]

Participants

Reactant 2

HCID 6140L-Phenylalanine

HCID 866563792,6,8-Trichloroquinoline-3-carboxylic acid

Product 1

HCID 452547512-((S)-1-Carboxy-2-phenyl-ethylamino)-6,8-dichloro-quinoline-3-carboxylic acidYield 39%

Procedure

In close analogy to the procedure described in Example 1, 2,6,8-trichloroquinoline-3-carboxylic acid is reacted with L-phenylalanine to provide the title compound in 39% yield as yellow needles (recrystallization from EtOH).

Sources & evidence

ORD record: ord-20ea73f8ae5c4a1dbcd3994d5ce31b27
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288549B2

Reaction notes

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