1,2-Dichloroethane → [[2-(Methoxymethylamino)-2-oxoethyl][(phenylmethoxy)carbonyl]amino]-acetic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of N-[(benzyloxy)carbonyl]-N-(carboxymethyl)glycine (28.45 g, 106.46 mmol) in DMF (163 mL) was added EDC (24.08 g, 125.62 mmol). The solution was cooled to 0° C. and treated with a mixture of N-methoxymethylamine hydrochloride (12.25 g, 125.62 mmol) and Hunig's base (21.88 mL, 125.62 mmol) in DMF (55 mL). The reaction was stirred at room temperature overnight and poured over a mixture of ice and aqueous 10% HCl solution. The mixture was extracted twice with EtOAc. The combined organics were washed twice with aqueous 10% HCl solution and once with brine, dried over Na2SO4, filtered, and concentrated in vacuo to afford a crude oil which was suspended in saturated aqueous NaHCO3 solution. The mixture was washed with EtOAc, adjusted to pH 2 with aqueous 1N HCl, and extracted three times with EtOAc. The final three organic extracts were combined, dried over MgSO4, filtered, and concentrated in vacuo to afford the product as a golden oil.

Provenance & Evidence