アジドぎ酸tert-ブチル 化学特性,用途語,生産方法
使用
t-Butyl azidoformate is a convenient reagent for the acylation of amines, hydrazines, and similar compounds.
製造方法
tert-Butyl chloroformate was prepared in solution as follows. Dry phosgene was introduced into a solution of 18 g (0.24 mol) of tert-butyl alcohol in 500 ml of anhydrous ether until about 52 g (0.5 mol) had been absorbed and the mixture was cooled in a Dry Ice-acetone bath. Then a solution of 20 g (0.28 mol) of pyridine in 200 ml of anhydrous ether was added dropwise with vigorous stirring. The reaction mixture was stored overnight in a Dry Ice box. The precipitated pyridine hydrochloride was filtered and the volume of the filtrate was reduced to -70 ml at reduced pressure with cooling in an icewater bath.This cold solution of tert-butyl chloroformate was added over 30 min to a vigorously stirred solution of 31.6 g (0.2 mol) of tetramethylguanidinium azide in 200 ml of chloroform; the temperature was kept at 0°C throughout the addition. The bath was removed and the reaction mixture stirred for an additional hour and then poured into 500 nil of ice water containing -2 ml of acetic acid. Extraction with two 60-ml portions of ether followed by careful evaporation of the dried (magnesium sulfate) organic phase gave tert-butyl azidoformate as a pale amber liquid in quantitative yield.
The Direct Preparation of tert-Butyl Azidoformate
Synthesis Reference(s)
Journal of the American Chemical Society, 81, p. 955, 1959
DOI: 10.1021/ja01513a049Tetrahedron Letters, 25, p. 3701, 1984
DOI: 10.1016/0040-4039(84)80109-4
安全性プロファイル
An unstable shockand
heat-sensitive explosive. It may explode
above 100°C and iptes at 143°C. When
heated to decomposition it emits toxic
fumes of NOx. See also AZIDES.
アジドぎ酸tert-ブチル 上流と下流の製品情報
原材料
準備製品
2-[[(1,1-ジメチルエトキシ)カルボニル]アミノ]-2-メチルプロパン酸
N-(tert-ブトキシカルボニル)-1,6-ジアミノヘキサン
N-(tert-ブトキシカルボニル)-L-メチオニン
N-(tert-ブトキシカルボニル)-4-ニトロ-L-フェニルアラニン
N,N'-ビカルバミン酸ジ-tert-ブチル
N-(tert-ブトキシカルボニル)-N-メチル-L-バリン
N-(tert-ブトキシカルボニル)-L-トレオニン
1,9-ビス-BOC-1,5,9-トリアザノナン
1-BOC-1,10-ジアミノデカン
N-BOC-サルコシンメチルエステル
BOC-1,4-ジアミノブタン塩酸塩
[[(1,1-ジメチルエトキシ)カルボニル]オキシ]カルバミン酸1,1-ジメチルエチル
N-BOC-ピロール