Water → HCID 57920995, compound

Participants

Reaction Steps

A solution of Boc-Mop-OH (0.42 g, 1.71 mmol), H-Gly-OBn.TsOH (0.64 g, 1.88 mmol), DCC (0.35 g, 1.71 mmol), HOBt.H2O (0.26 g, 1.71 mmol) and DIEA (0.89 mL, 5.13 mmol) in DMF (30 mL) was stirred at room temperature under Ar(g) for 20 h. The mixture was filtered to remove insoluble DCU and concentrated by rotary evaporation under high vacuum. The product was isolated by flash chromatography (two columns were needed; the first was run in 8:2 EtOAc/hexanes and the second in 7:3 EtOAc/hexanes) affording Boc-Mop-Gly-OBn (0.55 g, 82%) as a clear oil. 1H NMR (500 MHz, CDCl3, ˜3:2 ratio of 2 rotamers): δ7.41-7.32 (m, 5 H), 6.53 (app bs, 0.4 H), 5.22-5.15 (m, 2 H), 4.44 (dd, J=7.9, 5.6 Hz, 0.6 H); 4.31 (t, J=7.8 Hz, 0.4 H), 4.16-3.97 (m, 2.6 H), 3.93 (app bs, 0.4 H), 3.81-3.72 (m, 0.6 H), 3.53-3.43 (m, 1.4 H), 3.32 and 3.31 (overlapping s, 3 H), 2.49-2.42 (m, 0.6 H), 2.41-2.33 (m, 0.4 H), 2.16-2.05 (m, 1 H), 1.89 (bs, 0.6 H), 1.47 (s, 5 H), 1.42 (s, 4 H);

Provenance & Evidence