Hydrochloric Acid → HCID 66924919, compound

HRID 554355Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

Methyl 2-[(4-{[(tert-butoxycarbonyl) (methyl)amino]methyl}-2-phenyl-1H-pyrrol-1-yl)sulfonyl]benzoate (524 mg) was dissolved in tetrahydrofuran (5 mL) and methanol (3 mL), and 1 mol/L aqueous sodium hydroxide solution (3 mL) was added at 0° C. The mixture was stirred at 0° C. for 1 hr, and at room temperature for 16 hr, cooled again to 0° C., acidified with 1 mol/L hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=1:1→0:1) to give the title compound as a colorless amorphous (yield 256 mg, 50%).

Workup

waitat room temperature for 16 hr
temperaturecooled again to 0° C.
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=1:1→0:1)

Sources & evidence

ORD record: ord-94940b50a5724b34aed6803ad80e7324
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048909B2

Reaction notes

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