Acetic Anhydride → HCID 44464422, compound

Participants

Reaction Steps

The Cbz protected amino alcohol (XVII) (0.035 g, 0.076 mmol) was dissolved in 1 ml of anhydrous THF. To this triethylamine (0.11 mmol) was added dropwise. After 10 minutes acetic anhydride (0.11 mmol) was added and 1 mg of DMAP was added. The reaction mixture was stirred for 12 hrs and it was then washed with water. The organic layer was separated, dried (Na2SO4), and concentrated under reduced pressure. It was then subjected to silca gel chromatography with 2:1 hexane/ethyl acetate as eluent to give the acetylated amino alcohol (XVIII) as an oil. 0.028 g (73%). 1H NMR (500 MHz, CDCl3) δ 7.80-8.06 (m, 2H), 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), 2.07 (s, 3H). 13CNMR (125 MHz, CDCl3) 168.4, 155.85, 139.41, 139.36, 138.22, 135.43, 129.15, 128.68, 128.56, 128.37, 128.10, 127.72, 127.41, 127.64, 126.75, 125.62, 123.75, 80.23, 60.18, 54.14, 50.15, 47.99, 37.43, 17.1.

Provenance & Evidence