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0 °C

A solution of 2-tert-butoxycarbonylamino-3-(1H-imidazol-4-yl)-propionic acid benzyl ester (6.062 g, 17.57 mmol) and triethylamine (3.57 g, 4.90 mL, 35.14 mmol) in CHCl3 (50 mL) was cooled to 0° C. under argon. Trityl chloride (4.9 g, 17.57 mmol) in CHCl3 was added and after 20 minutes the solution became opaque. The solution was stirred at 0° C. overnight, warmed to room temperature, washed with water and brine, dried over MgSO4 and filtered. The solvent was removed and the crude material was chromatographed (silica gel, 25% EA/PE, Rf 0.78 75% EA/PE) to afford the title compound as a viscous gum (7.58 g, 74%). ESMS 588 (M+H+) 1H NMR (500 MHz, CDCl3) δ 1.42 (9H, s), 2.98 (1H, dd, J=4.65, 14.53 Hz), 3.05 (1H, dd, J=5.05, 14.53 Hz), 4.58 (1H, m), 5.02 (2H, d, J=2.55 Hz), 6.06 (1H, d, J=8.25 Hz), 6.47 (1H, s), 7.09 (6H, m), 7.26 (4H, m), 7.29 (10H, m), 7.36 (1H, s). 13C NMR (CDCl3) δ 28.11, 29.87, 53.61, 66.37, 74.95, 79.12, 119.30, 127.78, 128.16, 129.48, 135.29, 136.23, 138.48, 142.01, 155.34, 171.44.

1. temperaturewarmed to room temperature
2. washwashed with water and brine
3. dry with materialdried over MgSO4
4. filtrationfiltered
5. customThe solvent was removed
6. customthe crude material was chromatographed (silica gel, 25% EA/PE, Rf 0.78 75% EA/PE)