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The amino group in the structure of tert-butyl glycinate has a certain nucleophilicity and can undergo a series of nucleophilic substitution reactions, for example, it can be reacted with haloalkanes to obtain alkylated products. As a chemical intermediate, tert-butyl glycinate can be converted into a variety of organic compounds through a series of reactions, such as amino acids, peptides, heterocyclic compounds and so on. In the synthesis of amino acids, tert-butyl glycinate can be used as a starting material for the synthesis of other amino acids, and can be converted to the target product through nucleophilic substitution reaction, acylation reaction and other reactions.

Glycine tert-butyl ester is used in the preparation of Schiff base by reacting with benzophenone. The resultant Schiff base undergoes asymmetric alkylation with arylmethyl bromides in the presence of O-allyl-N-(9-anthracenylmethyl)cinchonidinium bromide as chiral phase transfer catalyst to give guanidine-containing pentacyclic compound.

10 mmol of glycine, 4 g of molecular sieves, and 20 mL of methyl tert-butyl ether were added to a 50 mL round-bottomed flask fitted with a septum, and the mixture was cooled to 25 °C. 30 mmol of sulfuric acid was slowly added dropwise to the solution using a syringe. The reaction was maintained at 25 °C for the indicated time as shown in Table 5. Upon completion of the reaction, the reaction mixture was quenched by slowly pouring it into 25 mL of saturated aqueous sodium bicarbonate solution. The organic phase was separated and the aqueous phase was extracted twice with hexane. The organic phases were combined, washed with water and subsequently dried with anhydrous sodium sulfate. Finally, the solvent was removed by distillation to give tert-butyl glycinate.

[1] Tetrahedron Letters, 2012, vol. 53, # 6, p. 641 - 645