Hydrochloric Acid → HCID 67044740, compound

HRID 1944445Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of {5-chloro-3-[2-(benzenesulfonyl)pyridin-2-ylmethyl]-3-methylindol-1-yl}acetic acid methyl ester (0.15 g) and tetrahydrofuran (1.3 mL) was treated with 5.0 M aqueous sodium hydroxide solution (1.7 mL), and the resulting mixture was stirred at 40° C. for 2 hours. The mixture was acidified by the addition of 5.0 M aqueous hydrochloric acid solution and extracted with ethyl acetate. The combined organic extract was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by preparative reverse-phase HPLC, eluting with a mixture of acetonitrile and water (2:3 to 9:1 by volume) to afford the title compound as a white solid (0.23 g).

Workup

extractionextracted with ethyl acetate
extractionThe combined organic extract
dry with materialwas dried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by preparative reverse-phase HPLC
washeluting with a mixture of acetonitrile and water (2:3 to 9:1 by volume)

Sources & evidence

ORD record: ord-56b6a7298ef844fe9d01cbf00e19e1e9
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394836B2

Reaction notes

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