Lithium Hexamethyldisilazide → HCID 11601657, compound

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Reaction Steps

The objective compound was prepared by the same procedure for the example 1, using a 4-chloro-2-(2-phenyl-propionyl amino)-benzoic acid methyl ester (1.00 g, 3.15 mmol) and LiHMDS (9.44 mmol, 1M solution in THF). After normal workup, the pure objective compound (0.54 g, 60%) was obtained as pale yellow solid by a flash column chromatography (Hex:EtOAc=4:1): 1H NMR (200 MHz, CDCl3) δ 1.86 (s, 3H, CH3), 6.94 (d, J=1.63 Hz, 1H, ArH), 7.06 (dd, J=8.55 Hz, 1.63 Hz, 1H, ArH), 7.26-7.32 (m, 5H, ArH), 7.83 (d, J=8.14 Hz, 1H, ArH), 9.21 (br s, 1H, NH); m.p. 174-175° C.; MS(EI) m/e 285 [M+], 153, 132, 104; HRMS m/e cacld. for C16H12NO2Cl 285.0557, found 285.0552.

Provenance & Evidence