Triethylamine → HCID 69598118, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 9-E (150 mg, 0.33 mmol), methyl (S)-(−)-2-isocyanato-3-phenylpropionate (120 μL, 0.66 mmol), and triethylamine (140 μL, 0.99 mmol) in dimethylformamide (2 mL) was stirred at 25° C. for 16 h. The reaction mixture was treated with Triamine-3 functionalized silica gel (1.2 mmol) and stirred for 1 h. The reaction mixture was filtered through a short plug of silica gel and washed with ethyl acetate (10 mL). The filtrate was concentrated and used without further purification. The crude product was dissolved in trifluoroacetic acid (10 mL) and heated at 70° C. for 16 h. The reaction mixture was concentrated and purified using preparative LCMS to yield the product (29 mg, 15%) as a white solid. 1H NMR (500 MHz, CD3OD): δ 7.83 (d, J=8.3 Hz, 2H), 7.42 (d, J=8.3 Hz, 2H), 2H), 7.31–7.28 (m, 2H), 7.25–7.22 (m, 1H), 7.18 (dd, J=8.3, 1.5 Hz, 2H), 7.02 (s, 1H), 4.53 (dd, J=7.8, 5.9 Hz, 1H), 4.44 (dd, J=7.3, 6.8 Hz, 1H), 3.69 (s, 3H), 3.19–3.04 (m, 4H), 3.00–2.94 (m, 2H), 1.42–1.35 (m, 2H), 1.34–1.28 (m, 2H), 1.24–1.19 (m, 2H), 0.90 (t, J=7.3 Hz, 3H); LCMS found for C28H35N4O7S (M+H)+: m/z=571.

Provenance & Evidence