Hydrochloric Acid → HCID 67044012, compound

HRID 1944393Notes

Reaction equation

C[O:2][C:3](=[O:35])[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[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[S:22](=[O:33])(=[O:32])[NH:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=[C:6]1[CH3:34].[OH-].[Na+].Cl>O1CCCC1>[F:14][C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[N:5]([CH2:4][C:3]([OH:35])=[O:2])[C:6]([CH3:34])=[C:7]2[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22](=[O:33])(=[O:32])[NH:23][CH2:24][C:25]1[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of (5-fluoro-3-{2-[(4-fluorophenyl)methylsulfamoyl]benzyl}-2-methylindol-1-yl)acetic acid methyl ester (0.22 g) and tetrahydrofuran (1.0 mL) was treated with 5.0 M aqueous sodium hydroxide solution (3.0 mL), and the resulting mixture was stirred at 40° C. for 3 hours. The mixture was acidified by the addition of 5.0 M aqueous hydrochloric acid solution and concentrated under reduced pressure. The residue was purified by preparative reverse-phase HPLC, eluting with a mixture of acetonitrile and water (3.5:6.5 to 9:1 by volume) to afford the title compound as a white solid (0.10 g).

Workup

concentrationconcentrated under reduced pressure
customThe residue was purified by preparative reverse-phase HPLC
washeluting with a mixture of acetonitrile and water (3.5:6.5 to 9:1 by volume)

Sources & evidence

ORD record: ord-f8427567a880465dab5eee1d41f3ce70
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394836B2

Reaction notes

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