Iminodiacetic acid → N-(Carboxymethyl)-N-((phenylmethoxy)carbonyl)glycine

Participants

Reaction Steps

To the solution of iminodiacetic acid XLV (10 g, 75.13 mmol) and K2CO3 (41.53 g, 300.52 mmol) in water (225 mL) was added a solution of CBzOsu (20.6 g, 82.64 mmol) in acetone (150 mL). The mixture was stirred at r.t. overnight. The acetone was evaporated under reduced pressure and the remaining water was washed with ethyl ether (2×). The aqueous layer was acidified to pH=2 with 2 M aq. HCl and then saturated with NaCl, washed with EtOAc (3×). The combined EtOAc was dried over MgSO4 and evaporated under reduced pressure to give 2-{[(benzyloxy)carbonyl](carboxymethyl) amino}acetic acid XLVI (15 g, 56.17 mmol, 75% yield). ESIMS found for C12H13NO6 m/z 290 (M+Na).

Provenance & Evidence