Tetrahydrofuran → HCID 21957316, compound

Participants

Reaction Steps

1.0 M LiOBu-t in THF (5 mL, 5 mmol) is added dropwise with stirring to a solution of acetic acid 1-(acetylamino-methyl)-2-chloro-ethyl ester (0.600 g, 3.10 mmol) in DMF (1 mL) and MeOH (0.127 mL) under nitrogen atmosphere at 0° C. [4-(4-Oxo-3,4-dihydro-2H-pyridin-1-yl)-phenyl]-carbamic acid benzyl ester (0.500 g, 1.55 mmol; prepared as described for Example 8), is added, and the mixture is allowed to gradually warm up to r.t. and stirred for additional 24 h. The mixture is quenched with saturated aq. NH4Cl (20 mL), diluted with aq. NaCl, and extracted with EtOAc (3×). The organic layers are combined and washed with brine, and dried over MgSO4. The solvent is removed under vacuum, and the crude product purified by silica gel flash chromatography (gradient 20% to 100% EtOAc—hexanes) to afford the title compound as a white solid. Yield 137 mg (26%). MS (m/z): 330 [M+H]+. 1H NMR (300 MHz, DMSO-d6) δ 8.24 (br. t, J=5.8 Hz, 1H), 7.72 (d, J=7.7, 1H), 7.53 (d, J=9.1, 2H), 7.27 (d, J=9.1, 2H), 4.97 (d, J=7.7 Hz, 1H), 4.72–4.67 (m, 1H), 4.10 (t, J=9.1 Hz, 2H), 3.75–3.69 (m, 1H), 3.40 (t, J=5.5 Hz, 2H), 2.50–2.49 (m, 2H), 1.82 (s, 3H).

Provenance & Evidence