(S)-2-benzyl-3-(tert-butoxycarbonylamino)propanoic acid(CAS: 189619-55-4)

(S)-2-Benzyl-3-(tert-butoxycarbonylamino)propanoic acid is a white crystalline solid with a molecular weight of approximately 331.43 g/mol. It has a pKa of around 4.5, indicating moderate acidity. The compound is poorly soluble in water but soluble in organic solvents like methanol and ethanol. Chemically, it is reactive towards nucleophiles, particularly amines, and can undergo esterification and amide formation under appropriate conditions.

(S)-2-Benzyl-3-(tert-butoxycarbonylamino)propanoic acid can be synthesized by protecting the amino group of 2-benzylpropanoic acid with tert-butoxycarbonyl (Boc) using di-tert-butyldicarbonate (BDDC) in the presence of a base like triethylamine. The reaction typically occurs under mild conditions, and the product can be isolated by column chromatography or recrystallization.

(S)-2-Benzyl-3-(tert-butoxycarbonylamino)propanoic acid finds applications in the pharmaceutical industry for the synthesis of peptide drugs. It is also used in the development of sensors and as a building block in polymer chemistry, particularly in the synthesis of biodegradable polymers. Its reactivity towards amines makes it valuable in organic synthesis and materials science.

When handling (S)-2-benzyl-3-(tert-butoxycarbonylamino)propanoic acid, it is essential to use appropriate personal protective equipment (PPE) such as gloves, goggles, and lab coats. Store the compound in a cool, dry place away from direct sunlight and heat sources. Use a fume hood during handling and synthesis to minimize exposure to volatiles. In case of spill, clean up with appropriate absorbents and dispose of according to local regulations. Refer to the Safety Data Sheet (SDS) for detailed information on handling and storage.