Diisopropylcarbodiimide → HCID 178454228, compound

Participants

Reaction Steps

To a mixture of compound 26A (468 mg, 1.11 mmol) and BOC-D-Phg-OH (11A, 280 mg, 1.11 mmol) was added anhydrous THF (10 mL) and the resultant mixture was stirred at rt for 5 min. DIPC (0.258 mL, 1.67 mmol) was added slowly at rt. The reaction mixture was stirred at rt overnight. Solvent was removed. The residua were dissolved in a small amount of ethyl acetate. Solid was removed by filtration. The filtrate was purified by silica column chromatography eluting with hexanes-ethyl acetate (v/v 3/1, 2/1, 1/1) to provide the title compound (27A, 275 mg) as an off-color foam-like powder in 37.8% yield. 1H NMR (CDCl3, 500 MHz) δ 10.74 (br s, 2H), 8.75 (s, 1H), 8.52 (s, 1H), 7.82 (d, 2H, J=8.0 Hz), 7.79 (s, 1H), 7.58 (d, 2H, J=8.5 Hz), 7.43 (m, 5H), 7.21 (dd, 1H, J=8.0, 2.0 Hz), 6.98 (d, 1H, J=9.0 Hz), 5.61 (d, 1H, J=6.5 Hz), 5.56 (s, 2H), 3.90 (d, 1H, J=12.5 Hz), 3.20 (t, 1H, J=12.0 Hz), 2.51 (m, 1H), 1.62 (m, 2H), 1.55-1.30 (m, 11H), 0.91 (m, 1H). LCMS (ESI) m/z 720.27 (MNa+), 676.17 (MNa+), 654.22 (MH+), 554.11, 345.17, 289.12 (100). HPLC: tR=5.55 min.

Provenance & Evidence