218916-64-4

基本信息
BOC-3-氨基-2-羥基丙酸
3-氨基-N-BOC-2-羥基丙酸
3-(BOC-氨基)-2-羥基丙酸
N-BOC-3-氨基-2-羥基丙酸
3-(叔丁氧羰基氨基)-2-羥基丙酸
BOC-DL-異絲氨酸BOC-3-AMINO-2-HYDROXYPROPIONIC ACID
N-β-(t-Butoxycarbonyl)-DL-isoserine
Boc-3-aMino-2-hydroxypropionic acid
3-(BOC-AMINO)-2-HYDROXYPROPANOIC ACID
3-(tert-Butoxycarbonylamino)-2-hydroxypropanoic acid
Propanoic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-hydroxy-
Propanoic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-hydroxy- (9CI)
3-[(tert-butoxycarbonyl)amino]-2-hydroxypropanoic-3-6-5(1)8/h1-2,6H,3-4H2
物理化學(xué)性質(zhì)
制備方法

632-12-2

24424-99-5

218916-64-4
以DL-異絲氨酸(1 g,9.52 mmol)和二碳酸二叔丁酯(2.7 g,12.37 mmol)為原料,合成N-Boc-3-氨基-2-羥基丙酸的一般步驟如下:將DL-異絲氨酸(1 g,9.52 mmol)溶解于叔丁醇(40 mL)和1 M NaOH水溶液(20 mL)的混合溶劑中,冰浴冷卻下緩慢加入二碳酸二叔丁酯(2.7 g,12.37 mmol)。反應(yīng)混合物在室溫下攪拌過夜。通過薄層色譜(TLC)監(jiān)測反應(yīng)進度,確認原料完全消耗后,于40℃水浴中減壓濃縮除去溶劑。隨后,用乙酸乙酯和1 M HCl進行三次液-液萃取,合并有機相并用飽和氯化鈉水溶液洗滌。有機層經(jīng)無水硫酸鎂干燥后,再次于40℃水浴中減壓濃縮,得到N-Boc-3-氨基-2-羥基丙酸(1.95 g,收率100%)。產(chǎn)物經(jīng)1H-NMR(500 MHz,CDCl3)表征,化學(xué)位移如下:δ 1.45(9H,s),3.51-3.65(2H,m),4.32(1H,m),5.10(1H,br)。
參考文獻:
[1] Patent: US2016/151506, 2016, A1. Location in patent: Paragraph 0284-0288
[2] Chemical and pharmaceutical bulletin, 2002, vol. 50, # 2, p. 239 - 252
[3] Journal of Medicinal Chemistry, 2014, vol. 57, # 22, p. 9447 - 9462
[4] Patent: WO2004/39814, 2004, A1. Location in patent: Page 111 - 112
[5] Patent: WO2011/146354, 2011, A1. Location in patent: Page/Page column 61