Trifluoroacetic acid → 2-(5-(N,N-dimethylsulfamoyl)-2,3-dioxoindolin-1-yl)acetic acid

HRID 571269Notes

Reaction equation

HRID 571269 reaction equation
[CH3:1][N:2]([CH3:25])[S:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][C:16]([O:18]C(C)(C)C)=[O:17])[C:10](=[O:23])[C:9]2=[O:24])(=[O:5])=[O:4].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][N:2]([CH3:25])[S:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][C:16]([OH:18])=[O:17])[C:10](=[O:23])[C:9]2=[O:24])(=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86681682tert-butyl 2-(5-(N,N-dimethylsulfamoyl)-2,3-dioxoindolin-1-yl)acetate

Product 1

HCID 866816832-(5-(N,N-dimethylsulfamoyl)-2,3-dioxoindolin-1-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 2-(5-(N,N-dimethylsulfamoyl)-2,3-dioxoindolin-1-yl)acetate (0.926 g, 2.51 mmol) and TFA (3 ml, 38.9 mmol) in DCM (10 ml) was stirred at room temperature for 4 hours. The volatiles were removed under vacuum affording 2-(5-(N,N-dimethylsulfamoyl)-2,3-dioxoindolin-1-yl)acetic acid which was used as such in the next step (1.29 g, 4.13 mmol).MS/ESI+ 312.9 [MH]+.

Workup

  1. customThe volatiles were removed under vacuum

Sources & evidence

ORD record
ord-8b2b8511ef13417dbabdb3f9fe16bbe3
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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