A Preparation of N-tert-Butoxycarbonyl L-Alanine

Purpose To demonstrate the protection of the amine group of an a-amino acid by forming a ferf-butyl carbamate. 

Di-ferf-butyl dicarbonate is a low-melting solid that is a liquid at or near room temperature and hydrolyzes readily to give ferf-butyl alcohol and carbon dioxide. Wear latex gloves when handling this chemical and do not breathe it or allow it to come in contact with your skin. If contact occurs, immediately flood the affected area with cold water and then rinse with 5% sodium bicarbonate solution. Dispense di-ferf-butyl dicarbonate only at a hood and minimize its exposure to atmospheric moisture by keeping the bottle tightly closed when not in use. 

The 3 M aqueous sodium hydroxide solution is caustic. Do not allow it to come in contact with your skin. If this should happen, wash the affected area with dilute acetic acid and then copious amounts of water. 

Diethyl ether is exfreme/y flammable and volatile, and its vapors can easily travel several feet along the bench top or the floor and then be ignited. Consequently, be certain there are no open flames anywhere in the laboratory whenever you are working with it. Use a flameless heating source whenever heating is required. 

Preparation Sign in at www.cengage.com/login to answer Pre-Lab Exercises, access videos, and read the MSDSs for the chemicals used or produced in this procedure. Review Sections 2.5, 2.10, 2.11, 2.13, 2.17, 2.21, and 2.29. 

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