Trifluoroacetic acid → 2-(5-(N-(2-morpholinoethyl)methylsulfonamido)-2,3-dioxoindolin-1-yl)acetic acid 2,2,2-trifluoroacetic acid salt

HRID 571326Notes

Reaction equation

CC1(C)CO[C:5]2([C:13]3[C:8](=[CH:9][CH:10]=[C:11]([N:14]([CH2:19][CH2:20][N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[S:15]([CH3:18])(=[O:17])=[O:16])[CH:12]=3)[N:7]([CH2:27][C:28]([O:30]C)=[O:29])[C:6]2=[O:32])[O:4]C1.[C:36]([OH:42])([C:38]([F:41])([F:40])[F:39])=[O:37]>C(OCC)(=O)C.CCCCCC>[F:39][C:38]([F:41])([F:40])[C:36]([OH:42])=[O:37].[O:24]1[CH2:25][CH2:26][N:21]([CH2:20][CH2:19][N:14]([C:11]2[CH:12]=[C:13]3[C:8](=[CH:9][CH:10]=2)[N:7]([CH2:27][C:28]([OH:30])=[O:29])[C:6](=[O:32])[C:5]3=[O:4])[S:15]([CH3:18])(=[O:17])=[O:16])[CH2:22][CH2:23]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of methyl 2-(5,5-dimethyl-5′-(N-(2-morpholinoethyl)-methylsulfonamido)-2′-oxospiro[[1,3]dioxane-2,3′-indoline]-1′-yl)acetate (0.450 g, 0.880 mmol) and TFA (0.678 ml, 8.80 mmol) in dioxane/water 1/1 (15 ml) was heated at 80° C. for 24 hours. Additional TFA (1.356 ml, 17.6 mmol) was added over 5 days with stirring at the same temperature. The volatiles were removed under vacuum, and the crude was triturated with diethyl ether. The insoluble was collected by filtration and dried under vacuum affording 2-(5-(N-(2-morpholinoethyl)methylsulfonamido)-2,3-dioxoindolin-1-yl)acetic acid 2,2,2-trifluoroacetic acid salt (0.319 g, 0.607 mmol, 69.0% yield, MS/ESI+ 412.0 [MH]+).

Workup

customThe volatiles were removed under vacuum
customthe crude was triturated with diethyl ether
filtrationThe insoluble was collected by filtration
customdried under vacuum

Sources & evidence

ORD record: ord-ac0f2e3ee7d04568840c391e2106b5d1
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09024027B2

Reaction notes

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