Trifluoroacetic acid → 2-(4-Cyano-1-oxoisoindolin-2-yl)-4-carbamoylbutanoic acid

HRID 906817Notes

Reaction equation

[C:1]([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][N:6]([CH:13]([CH2:21][CH2:22][C:23](=[O:25])[NH2:24])[C:14]([O:16]C(C)(C)C)=[O:15])[C:7]2=[O:12])#[N:2].FC(F)(F)C(O)=O>>[C:1]([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][N:6]([CH:13]([CH2:21][CH2:22][C:23](=[O:25])[NH2:24])[C:14]([OH:16])=[O:15])[C:7]2=[O:12])#[N:2]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 21988604Tert-butyl 2-(4-cyano-1-oxoisoindolin-2-yl)-4-carbamoylbutanoate

Product 1

HCID 219885622-(4-Cyano-1-oxoisoindolin-2-yl)-4-carbamoylbutanoic acidYield 89%

Procedure

A mixture of tert-butyl 2-(4-cyano-1-oxoisoindolin-2-yl)-4-carbamoylbutanoate (1.0 g, 2.91 mmol) and trifluoroacetic acid (5 mL) was stirred for 2 hours. The mixture was concentrated and the residue was crystallized from ether (15 mL) to give 2-(4-cyano-1-oxoisoindolin-2-yl)-4-carbamoylbutanoic acid (0.74 g, 89%) as a white solid: 1H NMR (DMSO-d6) δ 13.12 (b, 1H), 8.12 (d, J=7.6 Hz, 1H). 8.03 (d, J=7.6 Hz, 1H), 7.73 (t, J=7.6 Hz, 1H), 7.23 (s, 1H), 6.76 (s, 1H), 4.80-4.62 (m, 3H), 2.32-2.09 (m, 4H).

Workup

concentrationThe mixture was concentrated
customthe residue was crystallized from ether (15 mL)

Sources & evidence

ORD record: ord-5b70a9753b514efba7ecd2de996852e2
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012997B2

Reaction notes

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