Hydrochloric Acid → HCID 15283238, compound

Participants

Reaction Steps

To a room temperature suspension of Boc-Dap-OH (6.31 g, 22 mmol) in anhydrous CH2Cl2 (100 mL) was added HCl×Phe-OMe (5.2 g, 24.2 mmol), DEPC (6.7 mL, 44 mmol) and DIEA (11.5 mL, 65.9 mmol). This reaction mixture was stirred for 16 h, diluted with ethyl acetate (500 mL) and washed sequentially with 0.1 M HCl (2×300 mL), H2O (300 mL), saturated NaHCO3 (2×300 mL) and H2O (300 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo. This crude oil was purified by silica gel flash column chromatography using a 20-100% ethyl acetate/hexanes gradient. Boc-Dap-Phe-OMe was obtained as white foam (8.85 g, 19.7 mmol, 90% yield).

Provenance & Evidence