Sodium Chloride → Methyl (2-((tert-butoxycarbonyl)amino)ethyl)glycinate

Participants

Reaction Steps

To a solution of (2-aminoethyl)carbamic acid tert-butyl ester (from Step 6 below) (4.2 g, 26.3 mmol) in methylene chloride (50 mL) was added triethylamine (4.4 mL, 31.4 mmol) and methyl bromoacetate (2.4 mL, 26.3 mmol). The reaction was stirred overnight at room temperature. A saturated aqueous solution of sodium chloride (100 mL) was then added, and the organic layer was separated dried over MgSO4, filtered and concentrated. The residue was taken up in diethyl ether, and a saturated solution of HCl in diethyl ether was added to precipitate the product, which was filtered, and dried. It was recrystallized in ethanol/ethyl acetate, to give a white solid; 1.39 g (20% yield). MS-APCI: M+1=233.

Provenance & Evidence