Hydrochloric Acid → HCID 19789843, compound

Participants

Reaction Steps

To a suspension of methylglycinate hydrochloride (3.3 g, 26 mmol) in THF (100 mL) was added at 0° C. triethylamine (11 mL, 78 mmol). After stirring for 5 min, 1-naphthaloylchloride (4.5 mL, 31.5 mmol) was added dropwise and the resulting mixture was stirred overnight at room temperature. 10% HCl was added and the aqueous phase extracted with EtOAc. The combined organic phases were washed with 10% NaOH, brine and concentrated under vacuum. The crude compound was purified by flash chromatography using DCM/EtOAc (98:2) as eluent to give the compound 2a (5 g, 79%). 1H NMR (acetone-d6) δ 3.76 (s, 3H, OMe), 4.24 (d, J=6.0 Hz, 2H, CH2), 7.52-7.58 (m, 3H, Ar), 7.72 (dd, J=1.1 and 7.0 Hz, 1H, Ar), 7.90 (m, 1H, Ar), 8.01 (d, J=8.3 Hz, 2H, Ar), 8.46 (m, 1H, NH); 13C NMR (acetone-d6) δ 41.91 (CH2), 52.22 (OMe), 125.67, 126.07, 126.66, 127.09, 127.49, 128.99, 131.09, 131.22, 134.57, 135.36, 170.12 (CO), 171.13 (CO).

Provenance & Evidence