Water → HCID 44464416, compound

Participants

Reaction Steps

The Cbz protected amino alcohol (IX) (0.080 g, 0.19 mmol) was dissolved in 2 ml of ethanol and to this diketene (23 μL, 0.29 mmol) was added dropwise. The reaction mixture was then stirred for 1 hour and diluted with 4 ml dichloromethane. It was then poured into water and the organic layer was separated, and dried (Na2SO4). It was then subjected to silica gel chromatography with 2:1 hexane/ethyl acetate as an eluent to give the keto-amide (XI) as oil. 100 mg (98% yield) 1H NMR (500 MHz, CDCl3) δ 7.13-7.49 (m, 15H), 5.02-5.37 (m, 3H), 4.52-4.87 (m, 2H), 3.75-4.00 (m, 2H), 3.28-3.51 (m, 1H), 2.75-2.94 (m, 2H), 2.43 (s, 2H), 2.05 (s, 3H). 13CNMR (125 MHz, CDCl3) 201.2, 168.4, 155.85, 140.91, 140.36, 138.22, 129.15, 128.68, 128.56, 128.37, 128.10, 127.72, 127.41, 127.64, 126.75, 80.23, 60.18, 54.14, 50.15, 7.99, 43.6, 37.43, 25.7.

Provenance & Evidence