81196-09-0

基本信息
4-(BOC-氨基)苯乙酸
BOC-(4-氨基苯基)乙酸
4-(叔丁氧羰基氨基)苯乙酸
BOC-APH(4)-OH
BOC-4-APAC-OH
BOC-4-NHPHAC-OH
BOC-(4-AMINOPHENYL)ACETIC ACID
4-(Boc-aMino)phenylacetic acid
4-(T-Butoxycarbonylamino)phenylacetic acid
4-(T-BUTYLOXYCARBONYLAMINO)PHENYLACETIC ACID
4-(tert-Butoxycarbonylamino)benzeneacetic acid
4-(TERT-BUTYLOXYCARBONYLAMINO)-PHENYLACETIC ACID
物理化學(xué)性質(zhì)
制備方法

24424-99-5

1197-55-3

81196-09-0
通用方法:2-(4-((叔丁氧基羰基)氨基)苯基)乙酸(5)的合成。將4-氨基苯乙酸(4, 4g, 26.46mmol, 1當(dāng)量)溶解于二惡烷(52mL)和水(52mL)的混合溶劑中。在另一容器中,將碳酸鈉(2.8g, 26.42mmol, 1當(dāng)量)溶于水(25mL)中,攪拌并在冰浴中冷卻。將碳酸鈉溶液加入4-氨基苯乙酸的溶液中,隨后一次性加入二碳酸二叔丁酯(BOC-酐,6.24g, 28.59mmol, 1.1當(dāng)量)。反應(yīng)混合物在室溫下繼續(xù)攪拌4小時(shí)。反應(yīng)完成后,通過減壓蒸餾除去二惡烷。冷卻后的水層用乙酸乙酯覆蓋,并用稀KHSO4溶液酸化至pH4。隨后用乙酸乙酯進(jìn)行萃取,合并有機(jī)層,并通過柱層析(洗脫劑比例為1:1:1的乙酸乙酯-己烷-乙酸)純化,得到目標(biāo)化合物5(7.07g, 產(chǎn)率94%),為白色固體。1H-NMR(300MHz, CDCl3)數(shù)據(jù)如下:δ 7.29(d, J = 8.40Hz, 2H), 7.19(d, J = 8.47Hz, 2H), 3.70(s, 1H), 3.58(s, 2H), 1.52(s, 9H)。
參考文獻(xiàn):
[1] Journal of Medicinal Chemistry, 1998, vol. 41, # 13, p. 2361 - 2370
[2] Molecules, 2017, vol. 22, # 1,
[3] Patent: US6335445, 2002, B1. Location in patent: Page column 86-87
[4] Journal of Medicinal Chemistry, 2013, vol. 56, # 1, p. 254 - 263
[5] Patent: WO2014/85545, 2014, A1. Location in patent: Page/Page column 52; 53