Trifluoroacetic acid → HCID 86590808, compound

Participants

Reaction Steps

A solution of (4S,7S,11aS)-7-benzoylamino-6-oxo-1,3,4,6,7,8,11,11a-octahydro-2H-pyrido[1,2-a]azocine-4-carboxylic acid (2-ethoxy-5-oxo-tetrahydro-furan-3-yl)-amide, 45, (32 mg) in 10 mL of 1:1 acetonitrile/water is treated with 2 mL of trifluoroacetic acid. After stirring for 30 minutes the solution is concentrated in vacuo and the crude product purified by preparative reverse phase HPLC to afford 21 mg of the desired product as a white solid. 1H NMR (CD3OD) δ 7.92 (d, J=7.0 Hz, 2H), 7.54 (m, 3H), 5.75 (m, 1H), 5.63 (m, 1H), 5.42 (dd, J=8.1, 4.8 Hz, 1H), 5.01 (d, J=6.2 Hz, 1H), 4.72 (m, 1H0, 4.65 (d, J=4.0 Hz, 0.5H), 4.64 (d, J=4.0 Hz, 0.5 H), 4.31 (m, 1H), 3.18 (m, 1H), 2.68 (m, 2H), 2.45 (m, 3H), 2.26 (br d, J=13.9 Hz, 1H), 2.10 (m, 1H), 1.94 (m, 1H), 1.80 (br d, J=13.2 Hz, 1H), 1.61 (m, 2H); MS 442 (M+H)+.

Provenance & Evidence