Sodium Hydroxide → 5-(5-Methoxy-1,4,5,6-tetrahydrocyclopenta[d]imidazol-2-yl)-2,4-dimethylbenzoic acid

HRID 541470Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

Into around-bottom flask, was placed a solution of methyl 5-(5-methoxy-1,4,5,6-tetrahydrocyclopenta[d]imidazol-2-yl)-2,4-dimethylbenzoate (compound 461.6, 100 mg, 0.270 mmol, 1.00 equiv, 80%) in methanol (3 mL). A solution of sodium hydroxide (67.0 mg, 1.68 mmol, 5.00 equiv) in water (3 mL) was added and the resulting mixture was stirred overnight at 70° C., then concentrated in vacuo. The residue was diluted with water (3 mL) and the pH of the solution was adjusted to 2-3 with aqueous hydrogen chloride (12 M). The mixture was extracted ethyl acetate (3×10 mL), and the combined organics was concentrated in vacuo to obtain the title compound as a brown solid (80 mg, 84%).

Workup

customInto around-bottom flask, was placed
concentrationconcentrated in vacuo
additionThe residue was diluted with water (3 mL)
extractionThe mixture was extracted ethyl acetate (3×10 mL)
concentrationthe combined organics was concentrated in vacuo

Sources & evidence

ORD record: ord-9c9912a2557c42e682ce79e58e479847
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871790B2

Reaction notes

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