Glycine ethyl ester, hydrochloride → HCID 18363033, compound

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Reaction Steps

Ethyl N-(2-fluoro-4-nitrobenzoyl)glycinate triethylamine (0.85 ml, 6.1 mmol) was added to a solution of 2-fluoro-4-nitrobenzoic acid (T. R. Jones et al., UK Patent GB 2175 903A, 1986) (1.0 g, 5.4 mmol), glycine ethyl ester hydrochloride (0.85 g, 6.1 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.1 g, 5.7 mmol) in methylene chloride (30 ml). After stirring 1 hour at room temperature the solution was passed through a short pad of silica gel eluting with ethyl acetate: methylene chloride (1:3) and the resulting white solid was filtered from hexane and dried under high vacuum to give ethyl N-(2-fluoro-4-nitrobenzoyl)glycinate (1.04 g). 1H NMR (DMSO-d6, 300 MHz) δ: 1.22 (t, J=7 Hz, 3H, CH3), 4.05 (d, J=6 Hz, 2H, glyCH2), 4.15 (q, J=7 Hz, 2H, ester CH2), 7.88 (t, J=8 Hz, 1H, Ar), 8.17 (dd, J=8.5, 1.5 Hz, 1H, Ar), 8.25 (dd, J=10, 2 Hz, 1H), 9.09 (br t, J=5.5 Hz, 1H, CONH). Anal. Calculated for C1H11FN2O5 : C, 48.89; H, 4.10; N, 10.37. Found: C, 49.00; H, 4.11; N, 10.43.

Provenance & Evidence