3190-70-3

基本信息
(S)-4-異丁基惡唑烷-2,5-二酮
(S)-4-異丁基噁唑烷-2,5-二酮
(S)-(-)-4-異丁基氧氮雜環(huán)戊烷-2,5-二酮
L-Leu-NCA
L-Leucine NCA
L-Leucine N-Carboxanhydride
L-Leucine N-carboxyanhydride
N-Carboxy-L-leucine anhydride
(4S)-4-Isobutyloxazolidine-2,5-dione
(S)-4-ISOBUTYL-OXAZOLIDINE-2,5-DIONE
(S)-(-)-4-ISOBUTYLOXAZOLIDINE-2,5-DIONE
(S)-4β-(2-Methylpropyl)-2,5-oxazolidinedione
物理化學性質(zhì)
制備方法

75-44-5

61-90-5

3190-70-3
以光氣和L-亮氨酸為原料合成(S)-4-異丁基惡唑烷-2,5-二酮的一般步驟:將L-亮氨酸酰胺(HO-Leu-NH2,10.0g,76.2mmol)懸浮于150mL無水四氫呋喃(THF)中,加熱至50℃。向氨基酸懸浮液中緩慢加入20%光氣的甲苯溶液(76.0mL,152.4mmol)。約1小時后,氨基酸完全溶解,形成澄清溶液。將反應液在旋轉(zhuǎn)蒸發(fā)儀上濃縮,轉(zhuǎn)移至燒杯中,加入己烷使產(chǎn)物沉淀。通過過濾分離白色固體,并將其溶解于甲苯中。將甲苯溶液通過硅藻土床過濾以去除不溶性雜質(zhì)。向濾液中加入過量己烷以再次沉淀產(chǎn)物。通過過濾分離得到N-羧基-L-亮氨酸酐(Leu NCA),并在真空下干燥。最終獲得9.0g(收率75%)的Leu NCA,為白色結(jié)晶固體。其1H NMR(d6-DMSO)數(shù)據(jù)如下:δ9.13(1H),4.44(1H),1.74(1H),1.55(2H),0.90(6H)ppm。
參考文獻:
[1] Advanced Synthesis and Catalysis, 2004, vol. 346, # 9-10, p. 1247 - 1249
[2] Patent: US2008/274173, 2008, A1. Location in patent: Page/Page column 94
[3] Journal of the Chemical Society, 1950, p. 3222,3225
[4] Patent: US2789973, 1950,
[5] Nippon Kagaku Zasshi, 1956, vol. 77, p. 44,46