(R)-2-(N-benzyl-2-chloroacetamido)-3-hydroxypropanoic acid → (R)-4-Benzyl-5-oxo-3-morpholinecarboxylic Acid

Participants

Reaction Conditions

Reaction Steps

To a solution of (R)-2-(N-benzyl-2-chloroacetamido)-3-hydroxypropanoic acid (1.53 g, 5.63 mmol) in tert-butanol was added potassium tert-butanolate and the reaction mixture heated to 110° C. for three h, then cooled to room temperature and concentrated to dryness. The residue was acidified with 1 N HCl to pH 1 and the aqueous solution extracted with EtOAc (3×250 mL). The organic layer was dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, 10 to 30% CH3OH in CH2Cl2 with 1% acetic acid) to provide (R)-4-benzyl-5-oxomorpholine-3-carboxylic acid (780 mg, 59%) as a yellow foam. 1H NMR and MS consistent.

Provenance & Evidence