HCID 69223435, compound → HCID 69224175, compound

Participants

Reaction Conditions

Reaction Steps

2-[2,4-Dioxo-5-phenyl-3-[2-(trimethylsilyloxy)-1-ethoxymethylene]-2,3,4,5-tetrahydro-1H-1,5-diazepin-1-yl]-N-isopropyl-N-(4-methoxyphenyl)acetamide (12q) was combined with trifluoroacetic acid (10 mL) under argon and cooled to 0-5° C. After approximately 20 min., the reaction mixture was evaporated in vacuo. The residue was triturated with diethyl ether and hexane, filtered and dried under high vacuum to provide 2-[2,4-dioxo-3-(hydroxymethylene)-5-phenyl-2,3,4,5-tetrahydro-1H-1,5-diazepin-1-yl]-N-isopropyl-N-(4-methoxyphenyl)acetamide (12r, 0.927 g) as a solid. 1H NMR (400 MHz, CDCl3) 0.91 (d, J=2, 3H), 0.92 (d, J=2, 3H), 3.63 (m, 1H), 3.80 (s, 3H), 3.81 (d, J=17 Hz, 1H), 3.96 (d, J=17 Hz, 1H), 4.17 (dd, J=7, 12 Hz, 1H), 4.29 (dd, J=7, 12 Hz; 1H), 4.92 (m, 1H), 5.89 (d, J=6 Hz, 1H), 5.95 (d, J=6 Hz, 1H), 6.92 (m, 2H), 7.09 (m, 2H), 7.27 (m, 3H), 7.37 (m, 2H). MS (ESI) [M+Na]+=460

Provenance & Evidence