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

HRID 571229Notes

Reaction equation

CC1(C)CO[C:5]2([C:13]3[C:8](=[CH:9][CH:10]=[C:11]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH:12]=3)[N:7]([CH2:19][C:20]([O:22]C)=[O:21])[C:6]2=[O:24])[O:4]C1.C(O)(C(F)(F)F)=O>O1CCOCC1.O>[CH3:18][S:15]([NH:14][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:19][C:20]([OH:22])=[O:21])[C:6](=[O:24])[C:5]2=[O:4])(=[O:16])=[O:17]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of methyl 2-(5,5-dimethyl-5′-(methylsulfonamido)-2′-oxospiro[[1,3]dioxane-2,3′-indoline]-1′-yl)acetate (200 mg, 0.502 mmol) in dioxane/water 1:1 (7 ml) and TFA (0.193 ml, 2.510 mmol) was stirred at 80° C. overnight. TFA (0.271 ml, 3.51 mmol) was freshly added and stirring at 80° C. was continued for 24 hours. Then TFA (0.155 ml, 2.008 mmol) was freshly added and stirring at 80° C. was continued for additional 48 hours. The volatiles were removed under vacuum and the crude was purified by flash chromatography on silica gel (DCM:MeOH from 99.5:0.5 to 7:3+0.5% AcOH), affording 2-(5-(methylsulfonamido)-2,3-dioxoindolin-1-yl)acetic acid (143 mg, 0.479 mmol, 96% yield). MS/ESI+ 298.9 [MH]+.

Workup

stirringstirring at 80° C.
waitwas continued for additional 48 hours
customThe volatiles were removed under vacuum
customthe crude was purified by flash chromatography on silica gel (DCM:MeOH from 99.5:0.5 to 7:3+0.5% AcOH)

Sources & evidence

ORD record: ord-f07e96fcadba4013aa3c6b6f5df8e913
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09024027B2

Reaction notes

Loading…