Itaconic acid → (RS)-1-[2,5-difluoro-4-(3-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid

HRID 1823014Notes

Reaction equation

HRID 1823014 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)[C:5]([F:17])=[CH:4][C:3]=1[NH2:18].[C:19]([OH:27])(=[O:26])[C:20]([CH2:22][C:23](O)=[O:24])=[CH2:21]>>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)[C:5]([F:17])=[CH:4][C:3]=1[N:18]1[C:23](=[O:24])[CH2:22][CH:20]([C:19]([OH:27])=[O:26])[CH2:21]1

Participants

3

Reactant 2

HCID 811Itaconic acidHCID 219200542,5-Difluoro-4-(3-fluorobenzyloxy)-phenylamine

Product 1

HCID 21920043(RS)-1-[2,5-difluoro-4-(3-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acidYield 34.5%

Procedure

In an analogous manner to that described in Example 1a), 2,5-difluoro-4-(3-fluoro-benzyloxy)-phenylamine was reacted with itaconic acid to yield (RS)-1-[2,5-difluoro-4-(3-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid (34.5% of theory) as a grey solid; MS: m/e=363 (M−H)+.

Sources & evidence

ORD record
ord-6394382810ca4b699373ab238316a9d0
Source dataset
uspto-grants-2006_05
Patent number
US07037935B2

Reaction notes

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