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tert-Butyl carbazate is used in a palladium-catalyzed cross-coupling with vinyl halides to prepare N-Boc-N-alkenylhydrazines. It is utilized in solid phase peptide synthesis and in the optical purity determination of alfa-amino aldehyde. It reacts with aldehydes to get hydrazones, which finds application as an intermediate in the synthesis of HIV-1 protease inhibitors. In addition to this, it is used as a starting material for the preparation of BOC-azide, sulfonic and carboxylic hydrazides.
Protected hydrazine derivative, permitting selective reaction at one N atom, followed by mild acidic cleavage of the Boc group. For preparation of, e.g. N-aminosuccinimide, free from the cyclic hydrazide, see: J. Org. Chem., 37, 2040 (1972). Similarly, reaction with carbonyl or sulfonyl halides, followed by cleavage with HCl, provides a route to monoacyl hydrazides: Synthesis, 244 (1980). It is also commonly used in the synthesis of aza-amino acids; see, for example: Synthesis, 141 (1991) and references therein.
Monoalkylhydrazines can be prepared via reduction of Boc-hydrazones with borane-THF, and cleavage with HCl: J. Org. Chem., 46, 5413 (1981).
Precursor of the somewhat unstable tert-butyl azidoformate, useful for introduction of the Boc protecting group, see: Org. Synth. Coll., 5, 157 (1973). Caution! Possible violent decomposition of this azide on heating.
Karpenko, I. A.; Margathe, J. F.; Rodriguez, T.; Pflimlin, E.; Dupuis, E.; Hibert, M.; Durroux, T.; Bonnet, D. Selective Nonpeptidic Fluorescent Ligands for Oxytocin Receptor: Design, Synthesis, and Application to Time-Resolved FRET Binding Assay. J. Med. Chem. 2015, 58 (5), 2547-2552.
Kheirabadi, M.; Shi, L.; Bagheri, R.; Kabiri, K.; Hilborn, J.; Ossipov, D. A. In situ forming interpenetrating hydrogels of hyaluronic acid hybridized with iron oxide nanoparticles. Biomater. Sci. 2015, 3 (11), 1466-1474.
Gefahrenhinweise (EU): H228
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves and eye/face protection. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. In case of fire: Use for extinction: CO2, powder or water spray.