Dimethylformamide → HCID 118380176, compound

Participants

Reaction Steps

To a slurry of benzyl ((2R,3S)-1-(2,4-dimethoxybenzyl)-2-((5-((2-nitrophenyl)sulfonyl)-5,6-dihydropyrrolo[3,4-d][1,2,3]triazol-2(4H)-yl)methyl)-4-oxoazetidin-3-yl)carbamate (241 mg, −50%/wt, −0.178 mmol) and potassium carbonate (77.4 mg, 0.560 mmol) in DMF (3.0 mL) was added thiophenol (23.8 μl, 0.231 mmol). After stirring at rt for 2 h, Boc-anhydride (78 mg, 0.36 mmol) was added. After an additional 2 h, the slurry was diluted with EtOAc and washed with saturated NaHCO3 (aq). The aqueous layer was extracted with EtOAc (2×) and the combined organic layers were washed with LiCl (5% aq), brine, dried over Na2SO4 and concd in vacuo. The crude residue was combined with the residues from 2 like transformations (15 mg and 20 mg scales) and purified via silica gel chromatography (EtOAc-Heptane, 0-100%) to afford the title compound (85.5 mg, 81% combined). Rt=0.96 min, m/z=593.2 (M+1) Method 2m_acidic. 1H NMR (500 MHz, DMSO-d6) δ 8.21 (d, J=9.6 Hz, 1H), 7.40-7.27 (m, 5H), 6.92 (d, J=8.3 Hz, 1H), 6.49 (d, J=2.1 Hz, 1H), 6.40 (d, J=8.3 Hz, 1H), 5.04 (s, 2H), 5.00 (dd, J=9.6, 5.1 Hz, 1H), 4.65 (dd, J=14.0, 7.1 Hz, 1H), 4.56 (dd, J=4.1, 6.2 Hz, 1H), 4.38-4.24 (m, 5H), 4.12 (q, J=6.2 Hz, 1H), 3.86 (d, J=15.1 Hz, 1H), 3.74 (s, 3H), 3.72 (s, 3H), 1.46 (s, 9H).

Provenance & Evidence