4-Chloro-L-phenylalanine → 2-[(S)-1-Carboxy-2-(4-chloro-phenyl)-ethylamino]-6-chloro-quinoline-3-carboxylic acid

HRID 2065611Notes

Reaction equation

HRID 2065611 reaction equation
Cl[C:2]1[C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:15])[CH:8]=2)[N:3]=1.[Cl:16][C:17]1[CH:28]=[CH:27][C:20]([CH2:21][C@@H:22]([C:24]([OH:26])=[O:25])[NH2:23])=[CH:19][CH:18]=1>>[C:24]([C@@H:22]([NH:23][C:2]1[C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:15])[CH:8]=2)[N:3]=1)[CH2:21][C:20]1[CH:27]=[CH:28][C:17]([Cl:16])=[CH:18][CH:19]=1)([OH:26])=[O:25]

Participants

3

Reactant 2

HCID 7361904-Chloro-L-phenylalanineHCID 242660682,6-Dichloroquinoline-3-carboxylic acid

Product 1

HCID 452543742-[(S)-1-Carboxy-2-(4-chloro-phenyl)-ethylamino]-6-chloro-quinoline-3-carboxylic acidYield 63%

Procedure

In close analogy to the procedure described in Example 1, 2,6-dichloroquinoline-3-carboxylic acid is reacted with 4-chloro-L-phenylalanine to provide the title compound in 63% yield as yellow needles (recrystallization from EtOH/water).

Sources & evidence

ORD record
ord-84110fc197884cbab92f772f9fde777c
Source dataset
uspto-grants-2012_10
Patent number
US08288549B2

Reaction notes

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