Ethanol → (R)-ethyl 2-amino-5-(benzyloxycarbonylamino)pentanoate

Participants

Reaction Conditions

Reaction Steps

Boc-Orn(Z)—OH (1 equivalent, 0.4 g, 1.1 mmol) was dissolved in EtOH (4 mL). The reaction mixture was cooled at −10° C., and SOCl2 (1.5 equivalent, 119 μl, 1.65 mmol) was added dropwise. The mixture was allowed to warm to room temperature, then heated at 40° C. for 20 h (TLC control). The reaction mixture was concentrated and the crude was purified by flash chromatography (CH2Cl2/MeOH) to afford the compound 188 (178 mg, 55%) as a white solid Rf=0.23 (CH2Cl2/MeOH 90/10). 1H NMR (300 MHz, CDCl3): δ 7.37-7.27 (m, 5H), 5.54 (broad s, 1H), 5.05 (s, 2H), 4.17 (q, J=6.9 Hz, 2H), 3.95 (broad s, 1H), 3.30-3.13 (m, 2H), 2.10-1.85 (m, 2H), 1.85-1.55 (m, 2H), 1.22 (t, J=7.1 Hz, 3H).

Provenance & Evidence