Hydrochloric Acid → HCID 51051422, compound

HRID 1986475Notes

Reaction equation

N[C:2](=[O:35])[CH2:3][CH2:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:9]([CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[C:8]2[C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=1.[OH-].[Na+].C([OH:40])C.Cl>O>[C:23]([O:22][C:21]([NH:20][CH2:19][C:9]1[C:10]([CH2:15][CH:16]([CH3:18])[CH3:17])=[N:11][C:12]2[C:7]([C:8]=1[C:28]1[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=1)=[CH:6][C:5]([CH2:4][CH2:3][C:2]([OH:40])=[O:35])=[CH:14][CH:13]=2)=[O:27])([CH3:24])([CH3:25])[CH3:26]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of tert-butyl [6-(3-amino-3-oxopropyl)-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methylcarbamate (2.38 g, 5.0 mmol), 4N aqueous sodium hydroxide solution (12.5 ml, 50 mmol) and ethanol (20 ml) was stirred at 80° C. for 2 hrs. The reaction mixture was poured into water, neutralized with 1N hydrochloric acid and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give 3-[3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]propanoic acid (2.01 g, yield 84%) as white crystals.

Workup

extractionextracted with ethyl acetate
washThe extract was washed with 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

Sources & evidence

ORD record: ord-85cc1c4b2e294da19621e835484d28ca
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547710B2

Reaction notes

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