Itaconic acid → HCID 21920059, compound

Reaction equation

[F:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][O:7][C:8]2[N:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:17]([OH:25])(=[O:24])[C:18]([CH2:20][C:21](O)=[O:22])=[CH2:19]>>[F:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][O:7][C:8]2[N:13]=[CH:12][C:11]([N:14]3[C:21](=[O:22])[CH2:20][CH:18]([C:17]([OH:25])=[O:24])[CH2:19]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 811Itaconic acid

HCID 21920030HCID 21920030, compound

Product 1

HCID 21920059HCID 21920059, compoundYield 47%

Procedure

In an analogous manner to that described in Example 36 c), the reaction of 6-(4-fluoro-benzyloxy)-pyridin-3-ylamine with itaconic acid yields the crude (RS)-1-[6-(4-fluoro-benzyloxy)-pyridin-3-yl]-5-oxo-pyrrolidine-3-carboxylic acid as a green solid (yield 47% of theory).

Sources & evidence

ORD record: ord-dfef5276e5b94c1faca007560f456ca7
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07122562B2

Reaction notes

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