Triethylamine → 2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}ethyl 4-nitrobenzoate

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Reaction Steps

To a solution of 4-nitrobenzoylchloride (4.0 g, 21.6 mmoles) and N-(9-fluorenyl-methoxycarbonyl)ethanolamine (7.3 g, 25.9 mmoles) in 160 ml of methylene chloride is added triethylamine (3.1 ml, 22.6 mmoles). The mixture is stirred at room temperature for one hour, then is diluted with 400 ml of methylene chloride. The organic solution is washed with two portions of 200 ml of water and one portion of 200 ml of a saturated aqueous solution of sodium chloride. The organic phase is dried with Na2SO4, filtered and concentrated in vacuo. The resulting pale yellow solid is triturated in ethyl acetate. Filtration afforded 7.347 g of the title compound (79%). 400 MHz 1H NMR (DMSO-d6) δ: 8.32 (d, J=8.4 Hz, 2H), 8.20 (d, J=8.8 Hz, 2H), 7.87 (d, J=7.3 Hz, 2H), 7.66 (d, J=7.3 Hz, 2H), 7.61 (t, J=5.7 Hz, 1H), 7.39 (t, J=7.5 Hz, 2H), 7.28 (t, J=7.5 Hz, 2H), 4.4-4.3 (m, 4H), 4.20 (t, J=6.8 Hz, 1H), 3.45-3.35 (m, 2H). LCMS: 433 [M+H].

Provenance & Evidence