Dichloromethane → HCID 86635875, compound

Participants

Reaction Conditions

Reaction Steps

The keto amide (XI) (0.040 g, 0.08 mmol) was dissolved in 0.5 ml of acetonitrile and cooled to 0° C. To this tosyl azide (0.024 g, 0.12 mmol) was added followed by the addition of DBU (18 μL, 0.12 mmol) dropwise. The reaction mixture was stirred for 1 hr at 0° C. and then 3 hrs at room temperature. It was then concentrated under reduced pressure to give dark red oil. The residue was taken up in a minimum volume of dichloromethane and placed on a silica gel column. The compound was eluted with 2:1 hexane/ethyl acetate to give the diazo keto-amide (XII) as yellow oil. 0.033 g (78% yield). 1H NMR (500 MHz, CDCl3) δ 7.13-7.49 (m, 15H), 5.02-5.37 (m, 3H), 4.46-4.87 (m, 2H), 3.75-4.06 (m, 2H), 3.28-3.51 (m, 1H), 2.75-2.94 (m, 2H), 2.05 (s, 3H). 13CNMR (125 MHz, CDCl3) 171, 165.4, 155.85, 140.91, 140.36, 139.22, 129.14, 128.68, 128.26, 128.17, 128.10, 127.72, 127.41, 127.64, 126.75, 79.23, 60.38, 53.14, 50.15, 47.99, 45.6, 37.43, 26.6.

Provenance & Evidence