Hydrochloric Acid → HCID 66682554, compound

Participants

Reaction Steps

3-Amino-3-methoxycarbonylmethyl-azetidine-1-carboxylic acid tert-butyl ester (2 g; 8.2 mmol) dissolved in CH2Cl2 (100 ml) and triethylamine (3.4 ml; 24.5 mmol) is cooled to −5° C. Chlorocarbonyl-acetic acid ethyl ester (1.23 ml; 9.8 mmol) is slowly added under stirring. The reaction mixture is warmed to room temperature, stirred for 20 minutes, poured on 2N HCl (15 ml) and extracted with TBME three times. The organic phases are combined, washed with a saturated solution of NaHCO3, dried over Na2SO4 and evaporated to dryness. Chromatography (SiO2; Hexanes/acetone 7:3) yields the title compound as colorless crystals. 1H-NMR (400 MHz; DMSO-d6): 8.62 (s, 1H); 4.08 (q, 2H); 3.88 (m, 4H); 3.60 (s, 3H); 3.21 (s, 2H); 3.02 (s, 2H); 1.38 (s, 9H); 1.18 (t, 3H). MS (m/z) ES+: 359 (80; MH+); 303 (100);

Provenance & Evidence