Hydrochloric Acid → HCID 42644618, compound

HRID 1944385Notes

Reaction equation

C[O:2][C:3](=[O:34])[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][C:19]([S:22]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)(=[O:24])=[O:23])=[C:18]([F:32])[CH:17]=2)=[C:6]1[CH3:33].[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:34])=[O:2])[C:6]([CH3:33])=[C:7]2[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)(=[O:23])=[O:24])=[C:18]([F:32])[CH:17]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of {5-fluoro-3-[3-fluoro-4-(4-fluorobenzenesulfonyl)benzyl]-2-methylindol-1-yl}acetic acid methyl ester (0.14 g) and tetrahydrofuran (1.0 mL) was treated with 5.0 M aqueous sodium hydroxide solution (2.0 mL), and the resulting mixture was stirred at 40° C. for 1 hour. 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 (0.046 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-0f51a45bd84c45e9bd619862e6ecf8dd
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394836B2

Reaction notes

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