Triethylamine → HCID 67282364, compound

A mixture of 5-(methoxycarbonyl)-2-nitrobenzoic acid (0.12 g, 0.53 mmol), DMF (2.50 mL), triethylamine (0.22 mL, 1.6 mmol) and fluoro-N,N,N′,N′-tetramethylformamidinium hexafluorophosphate (0.17 g, 0.64 mmol) was stirred for 30 min and cumylamine (0.092 mL, 0.64 mmol) was added. The reaction mixture was stirred at rt for 1 d. Water was added and the mixture was extracted with EtOAc (2×). The combined organic phases were then washed with water, and brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash silica gel chromatography (50% to 100% EtOAc/hexanes) to afford methyl 4-nitro-3-[(2-phenylpropan-2-yl)carbamoyl]benzoate (0.13 g, 70%). LC-MS: (FA) ES+ 343.

1. stirringThe reaction mixture was stirred at rt for 1 d
2. extractionthe mixture was extracted with EtOAc (2×)
3. washThe combined organic phases were then washed with water, and brine
4. dry with materialdried over anhydrous Na2SO4
5. filtrationfiltered
6. concentrationconcentrated
7. customThe residue was purified by flash silica gel chromatography (50% to 100% EtOAc/hexanes)

ORD record

ord-73757c864cce4abdb9528c11d4bc6895

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08765773B2