4-Methylmorpholine → HCID 11340598, compound

Participants

Reaction Steps

[(S)-1-(2-Dimethylamino-ethylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester. HOBT (1.4 g, 10.7 mmol) and EDCl (2 g, 10.7 mmol) were added to a solution of (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid (2 g, 7.2 mmol) in DMF (36 mL). Following the addition of a solution of N′,N′-dimethyl-ethane-1,2-diamine (0.946 g, 10.7 mmol) in DMF (5 mL), N-methyl-morpholine (1.5 g, 14.4 mmol) was added dropwise. The reaction mixture was stirred at rt overnight. Water (50 mL) and EtOAc (70 mL) were then added to the mixture. The aqueous layer was extracted with EtOAc (3×70 mL). The combined organic layers were washed with 1 N NaOH (2×50 mL) and brine (50 mL), dried (MgSO4), and concentrated. Purification by column chromatography [0–20% (1% NH4OH/MeOH)/CH2Cl2] afforded 2.5 g (99%) of the desired product. MS (electrospray): mass calculated for C18H29N3O3, 335.22; m/z found, 336.1 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.02 (s, 1H), 7.32–7.28 (m, 2H), 7.25–7.20 (m, 3H), 6.24 (s, 1H), 5.23 (d, J=6.5 Hz, 1H), 4.32–4.30 (m, 1H), 3.23–3.19 (m, 2H), 3.09 (dd, J=13.5, 6.3 Hz, 1H), 2.98 (dd, J=13.5, 6.3 Hz, 1H), 2.31–2.15 (m, 4H), 2.10 (s, 6H), 1.41 (s, 9H).

Provenance & Evidence