Trifluoroacetic acid → 2-(4-(Methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetic acid

HRID 571280Notes

Reaction equation

HRID 571280 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[C:8](=[O:24])[N:9]([CH2:16][C:17]([O:19]C(C)(C)C)=[O:18])[C:10]2=[O:15])(=[O:4])=[O:3].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][S:2]([NH:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[C:8](=[O:24])[N:9]([CH2:16][C:17]([OH:19])=[O:18])[C:10]2=[O:15])(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86681686Tert-butyl 2-(4-(methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate

Product 1

HCID 866816892-(4-(Methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetic acidYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl 2-(4-(methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate (85 mg, 0.240 mmol) and TFA (370 μl, 4.80 mmol) in 5 ml of DCM was stirred at room temperature overnight. The mixture was evaporated to obtain 2-(4-(methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetic acid (72 mg, 0.240 mmol, 100% yield, MS/ESI+ 298.9 [MH]+) and used as such in the following reaction without further purification.

Workup

  1. customThe mixture was evaporated

Sources & evidence

ORD record
ord-f78943207b4041648280d178b1fcd774
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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