Chemical Properties
White to pale yellow lumps
Uses
Starting material for preparing BOC-azide, a reagent to introduce the BOC amino protection.
Uses
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.
Synthesis Reference(s)
Journal of the American Chemical Society, 82, p. 2725, 1960
DOI: 10.1021/ja01496a018Chemical and Pharmaceutical Bulletin, 18, p. 217, 1970
DOI: 10.1248/cpb.18.217
Purification Methods
Distil it in a Claisen flask with a water or oil bath at ca 80o. After a couple of drops have distilled, the carbazate is collected as an oil which solidifies to a snow white solid. It can be crystallised with 90% recovery from a 1:1 mixture of pet ether (b 30-60o) and pet ether (b 60-70o). [Carpino et al. Org Synth Coll Vol V 166 1973, Caprino et al. Org Synth 44 20 1964, Beilstein 3 IV 175.]
