Trifluoroacetic acid → HCID 86681755, compound

HRID 571338Notes

Reaction equation

HRID 571338 reaction equation
[CH3:1][S:2]([NH:5][CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[N:11]([CH2:17][C:18]([O:20]C(C)(C)C)=[O:19])[C:10]2=[O:25])(=[O:4])=[O:3].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][S:2]([NH:5][CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[N:11]([CH2:17][C:18]([OH:20])=[O:19])[C:10]2=[O:25])(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86681754HCID 86681754, compound

Product 1

HCID 86681755HCID 86681755, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(5-(methylsulfonamidomethyl)-1,3-dioxoisoindolin-2-yl)acetate (0.200 g, 0.543 mmol) in DCM (10 ml) cooled to 0° C., TFA (0.418 ml, 5.43 mmol) was added drop wise, and the solution stirred at room temperature for 24 hours. The solvent was removed under vacuum and dried to give 2-(5-(methylsulfonamidomethyl)-1,3-dioxoisoindolin-2-yl)acetic acid as a yellow solid (0.170 g, 0.544 mmol, yield considered to be quantitative, MS/ESI+ 312.9 [MH]+). This product was used without any further purification.

Workup

  1. customThe solvent was removed under vacuum
  2. customdried
  3. customto give

Sources & evidence

ORD record
ord-145fe551368e4f2eb3b630896e3f3b46
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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