[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([N+:14]([O-:16])=[O:15])=[C:9]([CH:13]=1)[C:10]([OH:12])=O)=[O:4].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.FC(N(C)C)=[N+](C)C.[C:39]([NH2:48])([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([CH3:41])[CH3:40]>O.CN(C=O)C>[N+:14]([C:8]1[CH:7]=[CH:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:13][C:9]=1[C:10](=[O:12])[NH:48][C:39]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([CH3:41])[CH3:40])([O-:16])=[O:15]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.
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