Hydrochloric Acid → (4-{[4-(2-tert-Butylphenyl)piperazin-1-yl]carbonyl}-2-methyl-1H-imidazol-1-yl)acetic acid

HRID 534998Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of methyl (4-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}-2-methyl-1H-imidazol-1-yl)acetate (Example 204, 0.18 g, 0.44 mmol) and 1 M LiOH solution (5 mL, 5.0 mmol) in tetrahydrofuran (5 mL) was stirred at 0° C. for 3 h. The reaction mixture was acidified with 1 M HCl solution and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound (0.14 g, 85%) as a white solid.

Workup

extractionextracted with ethyl acetate
washThe extract was washed with brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-e3568da04ef74b3ba174dfcd3590189e
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853215B2

Reaction notes

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