Hydrochloric Acid → (Z)-4-[4-(tert-butoxycarbonyl)piperazin-1-yl]-3-(prop-1-en-1-yl)benzoic acid

HRID 1038532Notes

Reaction equation

C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[C:7](/[CH:24]=[CH:25]\[CH3:26])[CH:6]=1)=[O:4].[OH-].[Na+].Cl>CO>[C:20]([O:19][C:17]([N:14]1[CH2:15][CH2:16][N:11]([C:8]2[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=2/[CH:24]=[CH:25]\[CH3:26])[CH2:12][CH2:13]1)=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

Conditions

Temperature: 50 °C

Procedure

tert-Butyl (Z)-4-[4-(methoxycarbonyl)-2-(prop-1-en-1-yl)phenyl]piperazine-1-carboxylate (96 mg, 0.267 mmol) was dissolved in methanol (3.0 mL). Under ice-cold conditions, 4N aqueous solution of sodium hydroxide (334 μL) was added, and the mixture was stirred at 50° C. overnight. Subsequently, 4N aqueous solution of sodium hydroxide (668 μL) was further added under ice-cold conditions, and stirred at 50° C. overnight. The reaction solution was added 4N aqueous solution of hydrochloric acid under ice-cold conditions, and extracted with chloroform. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/acetone). The title compound (108 mg (yield >99%)) was obtained as a white crystal.

Workup

stirringstirred at 50° C. overnight
extractionextracted with chloroform
washThe organic layer was washed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customThe obtained residue was purified by silica-gel column chromatography (hexane/acetone)

Sources & evidence

ORD record: ord-3ceba10f60914daeb4a0e3bc47586a46
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08551985B2

Reaction notes

Loading…