Hydrochloric Acid → 4-cyclobutyl-5-(5-ethyl-1H-imidazol-2-yl)-2-methylbenzoic acid

HRID 541395Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of methyl 4-cyclobutyl-5-(5-ethyl-1H-imidazol-2-yl)-2-methylbenzoate (compound 245.2, 200 mg, 0.600 mmol, 1.00 equiv, 90%) and sodium hydroxide (107 mg, 2.68 mmol, 4.00 equiv) in a solvent mixture of methanol and water (4/2 mL) was stirred for 3 h at 60° C. After cooling to ambient temperature, the pH was adjusted to 3-4 with hydrogen chloride (aq., 6 M). The resulting mixture was concentrated in vacuo to yield 150 mg of a white solid.

Workup

temperatureAfter cooling to ambient temperature
concentrationThe resulting mixture was concentrated in vacuo

Sources & evidence

ORD record: ord-e8ba5eb9f43c4a0da816bb09985611ce
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871790B2

Reaction notes

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