Hydrochloric Acid → 7-[5-(2-methoxyphenyl)-1H-imidazol-2-yl]heptanoic acid

HRID 1616550Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

Add a solution of sodium hydroxide (1.85 g, 46 mmol) in water (40 mL) to a solution of 7-[5-(2-methoxyphenyl)-1H-imidazol-2-yl]heptanoic acid methyl ester (5.84 g, 18.5 mmol) in methanol (30 mL) at room temperature under nitrogen and heat the mixture at 40° C. for 4.5 hours. Cool the mixture and treat with 1 N HCl (46 mL) and heat at reflux for 30 minutes. Collect the precipitate, wash with water (3×30 mL), and dry under reduced pressure for 12 hours. Triturate the solid with methylene chloride (50 mL) at reflux for 40 min and collect by filtration to provide 7-[5-(2-methoxyphenyl)-1H-imidazol-2-yl]heptanoic acid (4.27 g, 77%). APCI mass spectrum m/z 301 [C17H22N2O3—H]−.

Workup

temperatureCool the mixture
temperatureheat
temperatureat reflux for 30 minutes
customCollect the precipitate
washwash with water (3×30 mL)
customdry under reduced pressure for 12 hours
customTriturate the solid with methylene chloride (50 mL)
temperatureat reflux for 40 min
filtrationcollect by filtration

Sources & evidence

ORD record: ord-299f36c3da8d4c13b600b089abedbff5
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765796B2

Reaction notes

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