Trifluoroacetic acid → 2-(4-(N-(2-morpholinoethyl)-methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetic acid 2,2,2-trifluoroacetic acid salt

HRID 571290Notes

Reaction equation

HRID 571290 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][N:9]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[C:16](=[O:32])[N:17]([CH2:24][C:25]([O:27]C(C)(C)C)=[O:26])[C:18]3=[O:23])[S:10]([CH3:13])(=[O:12])=[O:11])[CH2:3][CH2:2]1.[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34]>C(Cl)Cl>[F:36][C:35]([F:38])([F:37])[C:33]([OH:39])=[O:34].[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][N:9]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[C:16](=[O:32])[N:17]([CH2:24][C:25]([OH:27])=[O:26])[C:18]3=[O:23])[S:10]([CH3:13])(=[O:12])=[O:11])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86681694tert-butyl 2-(4-(N-(2-morpholinoethyl)methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate

Product 1

HCID 866816952-(4-(N-(2-morpholinoethyl)-methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetic acid 2,2,2-trifluoroacetic acid salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl 2-(4-(N-(2-morpholinoethyl)methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate (256 mg, 0.548 mmol) and TFA (844 μl, 10.95 mmol) in DCM (5 ml) was stirred at room temperature for 48 hours. The mixture was evaporated and so obtained crude of 2-(4-(N-(2-morpholinoethyl)-methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetic acid 2,2,2-trifluoroacetic acid salt (MS/ESI+ 412 [MH]+) was used as such in the following reaction.

Workup

  1. customThe mixture was evaporated

Sources & evidence

ORD record
ord-e1abe8e7accf41889c19998a2295ce03
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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