tert-Butyl carbazate

Chemical properties

White to pale yellow lumps

The Uses of tert-Butyl carbazate

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.

The Uses of tert-Butyl carbazate

Starting material for preparing BOC-azide, a reagent to introduce the BOC amino protection.

Synthesis Reference(s)

Journal of the American Chemical Society, 82, p. 2725, 1960 DOI: 10.1021/ja01496a018
Chemical and Pharmaceutical Bulletin, 18, p. 217, 1970 DOI: 10.1248/cpb.18.217

Chemical property

Tert-Butyl carbazate is a chemical compound that functions as a reagent in the synthesis of various organic compounds. It acts as a carbonyl-protecting group in the preparation of aldehydes and ketones. Tert-Butyl carbazate reacts with carbonyl compounds to form hydrazones, which can be further manipulated to introduce different functional groups.
Tert-Butyl carbazate is particularly useful in the preparation of intermediates and agrochemicals. Its mode of action involves the formation of stable hydrazones, which can undergo subsequent transformations to yield the desired products. Tert-Butyl carbazate plays a role in the modification of carbonyl compounds, allowing for the introduction of specific chemical functionalities in a controlled manner.

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.]