Hydrochloric Acid → HCID 70564472, compound

HRID 1477846Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:15]2[C:23]3[C:18](=[C:19]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH:20]=[C:21]([F:24])[CH:22]=3)[CH:17]=[CH:16]2)([CH2:13][CH3:14])[C:9](OC)=[O:10])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:15]2[C:23]3[C:18](=[C:19]([NH:25][S:26]([CH3:29])(=[O:27])=[O:28])[CH:20]=[C:21]([F:24])[CH:22]=3)[CH:17]=[CH:16]2)([CH2:13][CH3:14])[CH2:9][OH:10])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of methyl 2-(4-chlorophenyl)-2-(6-fluoro-4-(methylsulfonamido)-1H-indol-1-yl)butanoate (0.5 g, 1.14 mmol) in THF (5 mL) was added dropwise lithium aluminum hydride solution (1.4 mL, 1 M in THF) at −78° C. The reaction mixture was stirred for 0.5 hours at −78° C. TLC and LCMS monitored the reaction was over, then 3M HCl solution was added carefully into the reaction to adjust pH=2˜3 in ice bath. The organic layer was separated and the aqueous layer was extracted with EA. The combined organic layer was washed with brine and dried over anhydrous sodium sulfate. The resulting mixture was filtered and concentrated in vacuo. The residue was purified by silica gel flash chromatography (PE: EA=2:1) to afford the title compound. LC/MS m/z=411.1 [M+H]+.

Workup

additionwas added carefully into the reaction
customThe organic layer was separated
extractionthe aqueous layer was extracted with EA
washThe combined organic layer was washed with brine
dry with materialdried over anhydrous sodium sulfate
filtrationThe resulting mixture was filtered
concentrationconcentrated in vacuo
customThe residue was purified by silica gel flash chromatography (PE: EA=2:1)

Sources & evidence

ORD record: ord-fe223d2169db4722a7a35f69023633e4
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403807B2

Reaction notes

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