Sodium Hydroxide → 4-Methyl-3-(3,4,6,7-tetrahydropyrano[3,4-d]imidazol-2-yl)benzoic acid

HRID 541187Notes

Reaction equation

[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][C:3]=1[C:12]1[NH:16][C:15]2[CH2:17][O:18][CH2:19][CH2:20][C:14]=2[N:13]=1.[OH-].[Na+]>CO.O>[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:12]1[NH:16][C:15]2[CH2:17][O:18][CH2:19][CH2:20][C:14]=2[N:13]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of methyl 4-methyl-3-(3,4,6,7-tetrahydropyrano[3,4-d]imidazol-2-yl)benzoate (compound 1.10, 210 mg, 0.73 mmol, 1.00 equiv, 95%) and sodium hydroxide (92.65 mg, 2.32 mmol, 3.00 equiv) in 12 mL methanol/H2O (2:1) was stirred for at 60° C. in an oil bath. After 2 h, the reaction mixture was concentrated under reduced pressure and the residue was taken up in 5 mL of H2O. The resulting mixture was washed with 3×10 mL of ethyl acetate and the pH of the aqueous layer was then adjusted to 2-3 using hydrogen chloride (aq., 2 M). The resulting mixture was extracted with 3×30 mL of ethyl acetate. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure to yield 0.21 g (89%) of the title compound as a white solid.

Workup

concentrationthe reaction mixture was concentrated under reduced pressure
washThe resulting mixture was washed with 3×10 mL of ethyl acetate
extractionThe resulting mixture was extracted with 3×30 mL of ethyl acetate
dry with materialThe combined organic layers were dried (Na2SO4)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-f3250afdd1464b609ee0434f1be87d50
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871790B2

Reaction notes

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