Water → HCID 57994310, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-3-(4-Benzyloxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid (10 g, 26.9 mmol) in DMF (100 ml) was added cyclopentanol (4.6 g, 53.8 mmol) and DMAP (329 mg, 2.69 mmol). The solution was cooled down to 0° C. and EDC.HCl (5.4 g, 28.2 mmol) was added. The reaction mixture was then stirred at r.t. for 22 hours. Water (100 ml) and EtOAc (100 ml) were added and the phases were separated. The aqueous phase was extracted with EtOAc (2×80 ml). The organics were washed with water (3×50 ml) and brine (50 ml), then dried over magnesium sulfate, filtered and evaporated in vacuo. The crude product was purified on column (Heptane/EtOAc 7:3) to yield the title compound (8.09 g, 68.4%). LCMS purity 96.6%, m/z 462 [M++Na]+.

Provenance & Evidence