p-Toluenesulfonic acid → HCID 15520896, compound

Participants

Reaction Steps

Ethyl acrylate (24.4 mL, 225 mmol) and glycine, benzyl ester, p-toluenesulfonate (50.0 g, 148 mmol) were combined in a 250 mL round bottom flask. With stirring, triethylamine (24.8 mL, 178 mmol) was added via syringe and the reaction mixture was stirred at room temperature for 22 hours. The reaction mixture was partitioned between ethyl acetate (660 mL) and 10% aqueous Na2CO3 (300 mL). The organics were washed with water (100 mL) and saturated NaCl (100 mL). The organics were dried over MgSO4, filtered and concentrated in vacuo followed by pumping under high vacuum to yield N-(carbobenzyloxymethyl)-3-aminopropionic acid, ethyl ester (39.3 g, 73% yield) as a yellow oil.

Provenance & Evidence