Hydrochloric Acid → HCID 11515541, compound

Participants

Reaction Steps

A solution of LDA in heptane/THF/ethylbenzene (1.8 M, 13.2 mL, 24 mmol) was added to a solution of methyl N-benzyl-N-(3-chloro-4-fluorophenyl)glycinate (7-2, 4.08 g, 13.2 mmol) in THF (100 mL) at −78° C. and stirred for 20 minutes before adding ethyliodide (10.6 g, 132 mmol, 10.0 equiv). The mixture was allowed to reach 23° C. as it stirred for 18 h. The reaction mixture was acidified with saturated aqueous ammonium chloride (100 mL), ammonium chloride (1.42 g, 26.5 mmol, 2.00 equiv), and concentrated HCl (1 mL). The product was extracted with EtOAc. The organic layer was washed with saturated ammonium chloride, H2O, and brine before drying with MgSO4 and concentrating. The residue was purified by flash column chromatography (SiO2, 0-11% EtOAc/hexanes gradient) to give a clear light-yellow oil, (7-3). 1H NMR (300 MHz, CDCl3) δ 7.33-7.20 (m, 5H), 6.91 (dd, J=8.9, 8.9 Hz, 1H), 6.80 (dd, J=6.1, 3.1. Hz, 1H), 6.60 (ddd, J=9.2, 3.2, 3.2 Hz, 1H), 4.60 (d, J=17.4 Hz, 1H), 4.47 (d, 17.4 Hz, 1H), 4.22 (t, J=7.5 Hz, 1H), 3.69 (s, 3H), 2.08-1.94 (m, 1H), 1.93-1.78 (m, 1H), 1.00 (t, J=7.5 Hz, 3H).

Provenance & Evidence