Hydrochloric Acid → {5-Fluoro-3-[3-(4-fluorobenzenesulfonyl)thiophen-2-ylmethyl]-2-methylindol-1-yl}acetic acid

HRID 1944379Notes

Reaction equation

C[O:2][C:3](=[O:32])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([F:14])=[CH:11][CH:12]=2)[C:7]([CH2:15][C:16]2[S:17][CH:18]=[CH:19][C:20]=2[S:21]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)(=[O:23])=[O:22])=[C:6]1[CH3:31].O1CCCC1.[OH-].[Na+].Cl>CO>[F:14][C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[N:5]([CH2:4][C:3]([OH:32])=[O:2])[C:6]([CH3:31])=[C:7]2[CH2:15][C:16]1[S:17][CH:18]=[CH:19][C:20]=1[S:21]([C:24]1[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=1)(=[O:23])=[O:22]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of {5-fluoro-3-[3-(4-fluorobenzenesulfonyl)thiophen-2-ylmethyl]-2-methylindol-1-yl}acetic acid methyl ester (0.17 g), tetrahydrofuran (2.0 mL) and methanol (1.0 mL) was treated with 5.0 M aqueous sodium hydroxide solution (1.5 mL), and the resulting mixture was stirred at 40° C. overnight. The mixture was acidified by the addition of 5.0 M aqueous hydrochloric acid solution and concentrated to low bulk under reduced pressure. The resulting precipitate was collected by filtration, washed with water and dried to afford the title compound as a cream solid (0.11 g).

Workup

concentrationconcentrated to low bulk under reduced pressure
filtrationThe resulting precipitate was collected by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-99e7edbf59c149988f26d85e1a418bad
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394836B2

Reaction notes

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