Trifluoroacetic acid → 2-(6-Morpholino-2,3-dioxoindolin-1-yl)acetic acid

HRID 571263Notes

Reaction equation

HRID 571263 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:15]=[C:14]3[C:10]([C:11](=[O:25])[C:12](=[O:24])[N:13]3[CH2:16][C:17]([O:19]C(C)(C)C)=[O:18])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:15]=[C:14]3[C:10]([C:11](=[O:25])[C:12](=[O:24])[N:13]3[CH2:16][C:17]([OH:19])=[O:18])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86681677Tert-butyl 2-(6-morpholino-2,3-dioxoindolin-1-yl)acetate

Product 1

HCID 866816782-(6-Morpholino-2,3-dioxoindolin-1-yl)acetic acidYield 98.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(6-morpholino-2,3-dioxoindolin-1-yl)acetate (0.400 g, 1.155 mmol) in DCM (10 ml), TFA (1.716 ml, 23.10 mmol) was added drop wise. The resulting red solution was stirred at room temperature overnight. The volatiles were evaporated under vacuum to afford 2-(6-morpholino-2,3-dioxoindolin-1-yl)acetic acid (0.330 g, 1.137 mmol, 98% yield). MS/ESI+ 291.1 [MH]+.

Workup

  1. customThe volatiles were evaporated under vacuum

Sources & evidence

ORD record
ord-ef4fd2cb4f8a461c85f30b1a9ff85ee2
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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