Cyclohexanol → HCID 131731108, compound

Participants

Reaction Steps

EDC.HCl (7.5 g, 40 mmol) was added to a stirring solution of Boc-Thr(Bzl)-OH (10 g, 32 mmol), cyclohexanol (5.0 mL, 48 mmol), and OMAP (0.66 g, 5.3 mmol) in OCM (75 mL) at 0° C. The mixture was warmed to room temperature (rt) over 30 min and stirred additionally overnight. After removal of the solvent in vacuo, the residue was dissolved in AcOEt, washed successively with 5% citric acid (3×), 5% NaHCO3 (3×) and saturated NaCl (3×), dried over MgSO4, and concentrated in vacuo. The resulting oil was purified by silica gel column chromatography (AcOE:hexane 1:8) to yield oily Boc-Thr(Bzl)-OcHex (12 g, 30 mmol, 95%). 1H NMR (CDCl3 400 MHz) 67.34-7.25 (m, 5H), 5.28 (d, J=9.6 Hz, 1H), 4.83-4.77 (m, 1H), 4.54 (d, J=11.6 Hz, 1H), 4.38 (d, J=11.6 Hz, 1H), 4.26 (dd, J=2.2, 9.6 Hz, 1H), 4.15 (dq, J=2.2, 6.4 Hz, 1H), 1.84-1.81 (m, 1H), 1.78-1.62 (m, 4H), 1.56-1.46 (m, 1H), 1.45 (s, 9H), 1.44-1.28 (m, 4H), 1.26 (d, J=6.4 Hz, 3H).

Provenance & Evidence