O-Benzyl-D-serine → 2-((R)-2-Benzyloxy-1-carboxy-ethylamino)-6-chloro-quinoline-3-carboxylic acid

HRID 2065607Notes

Reaction equation

HRID 2065607 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.[CH2:16]([O:23][CH2:24][C@H:25]([C:27]([OH:29])=[O:28])[NH2:26])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH2:16]([O:23][CH2:24][C@@H:25]([NH:26][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)[C:27]([OH:29])=[O:28])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 112114O-Benzyl-D-serineHCID 242660682,6-Dichloroquinoline-3-carboxylic acid

Product 1

HCID 452541812-((R)-2-Benzyloxy-1-carboxy-ethylamino)-6-chloro-quinoline-3-carboxylic acidYield 34%

Procedure

In close analogy to the procedure described in Example 1, 2,6-dichloroquinoline-3-carboxylic acid is reacted with O-benzyl-D-serine to provide the title compound in 34% yield as yellow needles (recrystallization from DMF/water).

Sources & evidence

ORD record
ord-85312199da0c47b5a07bbe78d0550ea6
Source dataset
uspto-grants-2012_10
Patent number
US08288549B2

Reaction notes

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