Hydrogen Peroxide → Methyl 5-carbamoyl-4-cyclobutyl-2-methylbenzoate

To an 8-mL vial was added methyl 5-cyano-4-cyclobutyl-2-methylbenzoate (152.4, 100 mg, 0.436 mmol, 1.0 equiv), potassium carbonate (181 mg, 1.31 mmol, 3.0 equiv) and DMSO (2.2 mL) and stirring was initiated. Hydrogen peroxide (50 wt %) (176 μL, 3.05 mmol, 7.0 equiv) was added over about 1 minute. The mixture was stirred at room temperature for 29 hours then diluted into brine (10 mL) plus 1 M H3PO4 (1.5 mL). The mixture was extracted with ethyl acetate (10 mL×1, 3 mL×1). The combined organic layers were washed with brine (10 mL) plus a few drops of 1 M H3PO4 followed by a mixture of water (10 mL) plus saturated NaHCO3 (1 mL) and finally brine (5 mL). The organics was dried (Na2SO4), filtered and evaporated to obtain the title compound as a white solid (59 mg, 55%). m/z (ES+) 248.0 (M+H)+.

1. stirringThe mixture was stirred at room temperature for 29 hours
2. extractionThe mixture was extracted with ethyl acetate (10 mL×1, 3 mL×1)
3. washThe combined organic layers were washed with brine (10 mL) plus a few drops of 1 M H3PO4
4. additionfollowed by a mixture of water (10 mL) plus saturated NaHCO3 (1 mL) and finally brine (5 mL)
5. dry with materialThe organics was dried (Na2SO4)
6. filtrationfiltered
7. customevaporated

ORD record

ord-a209a3c19c424f0584a4d5a83e17febb

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871790B2