Sodium Hydroxide → (E)-3-[2-n-Butyl-1-[(2-chlorophenyl)methyl]-4-hydroxymethyl-1H-imidazol-5-yl]-2-benzyl-2-propenoic acid

HRID 1033895Notes

Reaction equation

[CH2:1]([C:5]1[N:6]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[Cl:40])[C:7](/[CH:19]=[C:20](\[CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)/[C:21]([O:23]CC)=[O:22])=[C:8]([CH2:10][O:11][Si](C(C)(C)C)(C)C)[N:9]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>C(O)C>[CH2:1]([C:5]1[N:6]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[Cl:40])[C:7](/[CH:19]=[C:20](\[CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)/[C:21]([OH:23])=[O:22])=[C:8]([CH2:10][OH:11])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of ethyl (E)-3-[2-n-butyl-1-{(2-chlorophenyl)methyl}-4-t-butyldimethylsilyloxymethyl-1H-imidazol-5-yl]-2-benzyl-2-propenoate (167 mg, 0.287 mmol) in absolute ethanol (3 mL) was treated portionwise at 6 hour intervals with 10% sodium hydroxide solution (3×1 mL). After being stirred overnight at 25° C., the reaction was heated to 50° C. for 4 hours, then concentrated in vacuo. The residual product was take0 up in water, acidified to pH 5-6 and extracted with methylene chloride. The isolated, dried, concentrated product was triturated with methanol/ether to provide 78 mg (62%) of the title compound; mp 176°-179° C. (d).

Workup

temperaturethe reaction was heated to 50° C. for 4 hours
concentrationconcentrated in vacuo
extractionextracted with methylene chloride
customThe isolated, dried
customconcentrated product was triturated with methanol/ether

Sources & evidence

ORD record: ord-cdb77ad93e654bcba0c8491fb75a4355
Source dataset: uspto-grants-1994_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05312828

Reaction notes

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