6404-29-1 6-((叔丁氧基羰基)氨基)己酸

WGK Germany:3 F:21 危险等级:IRRITANT 海关编码:29241990 存储类别:11 - 可燃固体

• 叔丁氧羰酰基6-氨基己酸可用于制备新型奥克梯隆型皂苷元荧光探针。
• 制备工艺 将10mol％NHPI加入25mL Schlenk反应管中，真空干燥15分钟，鼓入氧气，在氧气氛围下依次加入乙腈2mL，6-(叔丁氧基氨基)己醛1.0当量，连接一个氧气球，在反应管上加上玻璃塞后放入油浴锅中，50℃反应3h。反应完成后，减压浓缩，柱层析分离，洗脱剂为石油醚/乙酸乙酯/二氯甲烷(v:v:v＝3:1:1)，得到6-(叔丁氧基氨基)己酸收率92％。

医药

合成路线 1（1. 合成：6404-29-1）

产率：100% 合成条件：at 20℃; for 16 h; 实验步骤：向6-氨基庚酸（20g，15 3mmol）的二氯甲烷（30mL）溶液中加入二碳酸二叔丁酯（3 67g，16 8mmol）。将反应在室温下搅拌16小时。 过滤，减压除去溶剂。粗产物在高真空下干燥，得到408g（115％）所需产物400MHz 1H NMR（DMSOd6）δ285（q，J = 13 2,68Hz， 2H），2 15（t，J = 1 2 Hz，2H），1 47-1 43（m，4H），1 34（s，9H），1 22-1 18（m，2H）LCMS = 232 [M + H] 参考文献：

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合成路线 2（2. 合成：6404-29-1）

产率：97% 合成条件：With triethylamine In 1,4-dioxane; water at 20℃; for 23 h; Inert atmosphere 实验步骤：步骤A.合成jY-Boc-氨基酸烷基链（Boc-aa，m = 5或10）将市售氨基酸烷基链（7.77mmol）的水和二恶烷溶液在室温下搅拌。缓慢加入三乙胺（11.65mmol），然后加入Boc-ON（8.54mmol）。将溶液在氮气下保持23小时。然后，将混合物用乙醚和水稀释，然后用水（6x）洗涤。然后合并水层，缓慢加入几滴10％HCl水溶液，使pH达到2.5。然后将所得溶液用二氯甲烷（3x）洗涤。用饱和氯化钠盐溶液洗涤有机层。用硫酸镁干燥有机相，过滤并蒸发。进行快速色谱（己烷：丙酮，4：1），得到无色黄色粘稠油状物，收率97％.6-Boc-氨基 - 己酸（Boc-aa，m = 5）IR（NaCl，vmax，cm -1） ）：3339（NH），2860-3100（OH），1711（2x C = O），1527和1250（CNH），1173（COC）.1H-NMR（CDCl3，Jppm）：8.91（1H，br s， COOH），4.74（1H，s，NH），3.02（2H，m，CH2NH），2.27（2H，t，J = 7.4Hz，CH2COOH），1.24-1.68（6H，Nom，3×CH2）， 1.37（s，9H，3×CH3）.13C-NMR（CDCl3，.ppm）：178.7（COOH），156.4（OCONH），79.4（（CH3）3C），40.5（NHCH2），34.1（CH2COOH） ，29.8（NHCH 2 CH 2），28.6（3×CH 3），26.4（CH 2 CH 2 CH 2 CH 2 CH 2），24.5（CH 2 CH 2 COOH）.ESI + HRMS：[M + Na] + C 11 H 28 NNaO 4的计算值= 254.1363;实测值= 254.1360。 参考文献：

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合成路线 3（3. 合成：6404-29-1）

产率：91% 合成条件：With sodium hydroxide In 1,4-dioxane; water; ethyl acetate 实验步骤：7.1。制备N-BOC-6氨基己酸在250ml圆底烧瓶中加入2.62g（0.02mol）6-氨基己酸（Aldrich），40ml二恶烷，25ml水和25ml 1.0N氢氧化钠解。将反应溶液冷却至0℃并加入4,583g（0.021mol）二碳酸二叔丁酯（BOC 2 O）（Aldrich）。将反应混合物在0℃下搅拌1.5小时，然后在真空下除去大部分溶剂，得到液体残余物。将该残余物溶于30ml乙酸乙酯中，冷却至0℃10分钟，然后加入5％磷酸氢钾溶液（约50-60ml）使溶液的pH值达到2-3。将反应溶液加入50ml水和30ml乙酸乙酯中。将水层与有机层分离，水层用三份30ml乙酸乙酯萃取。合并有机层，用两份75ml水洗涤，用NaSO 4干燥，过滤，减压除去溶剂，得到4.22g（0.0182mol，91％收率）N-BOC-6-氨基己酸。一种浓稠的黄油。 1 H NMR（CDCl 3）显示除了在1.48ppm（tBu组）的大单线态外，通常观察到的6-氨基己酸的峰。 参考文献：

• [1] Patent: US5326856, 1994, A [2] Patent: US5585468, 1996, A