tert.-Butyl aminocarbonate (tert.-butyloxycarbonyloxyamine)--a new acylating reagent for amines.
tert.-Butyl aminocarbonate (tert.-butyloxycarbonyloxyamine)--a new acylating reagent for amines.
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叔丁基氨基碳酸酯（叔丁氧基羰氧基胺）——一种新型胺酰化剂。
DOI：
10.1111/j.1399-3011.1984.tb02692.x
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发表时间：
1984
期刊：
影响因子：
--
通讯作者：
Wilson,IB
中科院分区：
文献类型：
--
作者：
Harris,RB;Wilson,IB
以羟胺和二叔丁基碳酸二酯(2)为原料，合成了叔丁基氨基碳酸酯(1，叔丁氧基甲氧基胺)。1在水或二氧六环水溶液中用于不同氨基酸或胺的酰化反应。1也是在这种情况下制备的，并用于直接酰化氨基酸。1与所研究的所有胺在水或50%(v/v)二恶烷中的反应速度是2的1.5-2.5倍。在pH 6.5(15M-1·min-1)条件下，L-苯丙氨酸的酰化反应速度约为pH 10(72M-1·min-1)时的20%。2不是pH 7.0以下的酰化试剂，在pH 8.3(4M-1·min-1)时的反应速率约为pH 9.3(39M-1·min-1)时的10%。高产率地获得了高纯度的BOC-氨基酸，并且可以用标准程序定量地去保护。
tert.‐Butyl amino carbonate (1,tert.‐butyloxycarbonyloxyamine) was prepared by reaction of hydroxylamine with di‐tert.‐butyl dicarbonate (2). 1 was used to acylate different amino acids or amines in water or in aqueous dioxane. 1 was also preparedin situand used to acylate amino acids directly. 1 reacted 1.5–2.5 times faster than 2 with all amines studied either in water or 50% (v/v) dioxane. Remarkably, 1 retained its ability to acylate amines even in acid solution; the rate of acylation of L‐Phe at pH 6.5 (15 M‐1˙ min‐1) was about 20% of the rate at pH 10 (72 M‐1˙ min‐1). 2 was not an acylating reagent below pH 7.0 and as expected, the rate at pH 8.3 (4 M‐1˙ min‐1) was about 10% of that at pH 9.3 (39 M‐1˙ min‐1). Pure BOC‐amino acids were obtained in high yield and could be quantitatively deprotected by standard procedures.