L-Glutamine → 2-(2,6-Dioxopiperidin-3-yl)phthalimidine

HRID 429215Notes

Reaction equation

[NH2:1][C@H:2]([C:8]([OH:10])=O)[CH2:3][CH2:4][C:5](=[O:7])[NH2:6].[O:11]=[C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14]N1C(CCC(O)=O)C(O)=O>>[O:11]=[C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][N:1]1[CH:2]1[CH2:3][CH2:4][C:5](=[O:7])[NH:6][C:8]1=[O:10]

Participants

Reactant 2

HCID 5961L-Glutamine

HCID 1861092-(1-Oxo-1,3-dihydro-2H-isoindol-2-yl)pentanedioic acid

Product 1

HCID 915852-(2,6-Dioxopiperidin-3-yl)phthalimidine

Procedure

In a further method, a dialdehyde is allowed to react with glutamine and the resulting 2-(1-oxoisoindolin-2-yl)glutaric acid then cyclized to yield a 1-oxo-2-(2,6-dioxopiperidin-3-yl)-isoindoline of Formula I:

Sources & evidence

ORD record: ord-6d81c8363bc246b1a4e186ada65e14de
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06316471B1

Reaction notes

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