An Improved Preparation of N²‐tert‐Butoxycarbonyl‐ and N²‐Benzyloxy‐carbonyl‐(S)‐2,4‐diaminobutanoic Acids

Abstract

Utilizing N‐benzyloxycarbonyl‐ (1a) and N‐tert‐butoxycarbonyl‐(S)‐glutamine (1b), a highly efficient and practical method for the synthesis of N ²‐benzyloxycarbonyl‐ and N ²‐tert‐butoxycarbonyl‐(S)‐2,4‐diaminobutanoic acids (2a and 2b) has been developed. Reaction of (S)‐glutamine derivatives with iodosobenzene diacetate in a mixture of THF‐water at 4°C afforded selectively protected (S)‐2,4‐diaminobutanoic acids in good yields.

Keywords:

• Non‐proteinogenic amino acids
• Hofmann rearrangement
• Protecting groups
• Iodosobenzene diacetate

Acknowledgment

This research was supported in part by the State Committee for Scientific Research (KBN), Grant No 6 PO5F 005 21.