Guanidine Hydrochloride → HCID 136028598, compound

Participants

Reaction Conditions

Reaction Steps

A solution of diethyl oxalate (21.06 g, 0.144 mol) and ethyl benzyloxyacetate (28.0 g, 0.144 mol) in dry tetrahydrofuran (200 ml) was treated at 22° C. with sodium hydride (6.34 g of a 60% dispersion in mineral oil, 0.158 mol). Ethanol (0.05 ml) was added and the resulting mixture stirred at 22° C. for 18 h. The tetrahydrofuran was then evaporated under reduced pressure and the residual orange syrup dissolved in a solution of sodium ethoxide (0.144 mol, prepared from 3.31 g of sodium) in ethanol (200 ml). Guanidine hydrochloride (14.6 g, 0.153 mol) was added and the resulting mixture heated at 60° C. for 7 h. Acetic acid (3 ml) was then added to the gel-like reaction mixture and the ethanol was removed under reduced pressure. The residual paste was triturated with a mixture of ethyl alcohol and dichloromethane (1:4), filtered and the filtrate concentrated under reduced pressure. Chromatography of the residue on silica gel (elution with a gradient of ethyl alcohol 0–15% in dichloromethane) followed by recrystallization from 1,2-dichloroethane gave 2.00 g (5% yield) of the title ester as a yellow solid. 1HNMR 400 MHz (DMSO-d6) δ (ppm): 1.18 (3H, t, J=7.0 Hz, CH3), 4.17 (2H, q, J=7.0 Hz, CH2), 4.90 (2H, s, OCH2), 6.55 (2H, broad s, NH2), 7.3–7.4 (5H, m, aromatics), 11.4 (1H, broad s, NH). Anal. Calcd for C14H15N3O4: C, 58.12; H, 5.22; N, 14.52. Found: C, 57.94; H, 5.11; N, 14.58.

Provenance & Evidence