Hydrochloric Acid → [(2-Acetoxy-ethyl)-ethoxycarbonylmethyl-amino]-acetic acid ethyl ester

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Reaction Steps

To N-(2-hydroxyethyl)iminodiacetic acid (2.0 g, 11.3 mmol) in 250 mL EtOH was added concentrated HCl (1 mL, 12 mmol). The mixture was stirred for 24 h at rt and concentrated. The residue was partitioned in diethyl ether (150 mL) and NaHCO3 (100 mL, 10% wt). After layer separation, the organic phase was washed with aqueous NaHCO3 (2×50 mL) and dried over Na2SO4 and concentrated and dried under high vacuum. To this crude product in dichloromethane (70 mL) and triethylamine (2.5 g, 24.7 mmol) and was added acetyl chloride (1.57 g, 20 mmol) dropwise. The mixture was stirred at rt for 2 h and diluted with ether (120 mL), washed with 1% NaHCO3 (3×70 mL) and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was chromatographed (Et2O/hexane) to afford a clear oil (1.4 g). 1H-NMR (CD3OD, 300 MHz) δ (ppm): 4.17-4.09 (m, 6H), 3.57 (s, 4H), 3.00 (t, J=5.7 Hz, 2H), 2.03 (s, 3H), 1.23 (t, J=7.1 Hz, 6H); 13C-NMR δ (ppm) 171.1, 170.9, 62.9, 60.5, 55.6, 52.7, 20.9, 14.2; (ESI) m/z: 276 (M+H+, 100).

Provenance & Evidence