Tetrahydrofuran → HCID 86601377, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of p-nitrophenylchloroformate (171 mg, 0.848 mmol) in THF (15 mL) cooled to −78° C. under N2 atmosphere was added Et3N (236 μL, 1.70 mmol). Then a suspension of the intermediate 129 (416 mg, 0.848 mmol) in THF (4.2 mL) was added via canula. The resulting yellow mixture was stirred at −78° C. for 1 h and at 0° C. for 1.5 h, heated at 40° C. for 16 h and cooled to r.t. Then, neat 4-(2-aminoethyl)morpholine (119 μL, 0.848 mmol) was added and the solution was stirred for 4 h, quenched by addition of MeOH. It was allowed to stir for 30 min. and concentrated. The resulting material was purified by flash chromatography using MeOH/DCM (3:97) affording the title compound 132 (165 mg, 30% yield). 1H NMR: (DMSO-d6) δ (ppm): 9.77 (s, 1H), 8.64 (bs, 1H), 8.56 (t, J=5.9 Hz, 1H), 7.90 (d, J=8.2 Hz, 2H), 7.60 (t, J=5.9 Hz, 1H), 7.50 (d, J=8.0 Hz, 2H), 7.50-7.48 (m, 2H), 7.45 (d, J=2.3 Hz, 1H), 7.30 (d, J=8.8 Hz, 1H), 7.17 (t, J=7.6 Hz, 1H), 7.12 (t, J=7.8 Hz, 1H), 6.90 (dd, J=8.2, 2.0 Hz, 1H), 4.67 (d, J=6.0 Hz, 2H), 3.56 (t, J=4.1 Hz, 4H), 3.31 (t, J=6.1 Hz, 2H), 3.16 (q, J=6.1 Hz, 2H), 2.39 (t, J=6.8 Hz, 4H), 1.42 (s, 9H). m/z: 647.7 (MH+).

Provenance & Evidence