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S-[2-(叔丁氧羰基氨基)乙基]-3-苯基丙酸硫酯类化合物脱除Boc保护基的反应研究 被引量:3

Study on the Deprotection of Boc Group of S-2-(tert-Butoxycarbonylamino)ethyl 3-Phenylpropanethioates
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摘要 报道了取代苯丙酸类化合物1a~1d与N-叔丁氧羰基-L-半胱氨酸甲酯(2)在双(2-氧代-3-噁唑烷基)次磷酰氯(BOP-C1)作用下,以79%~92%收率得到缩合产物S-[2-(叔丁氧羰基氨基)乙基]-3-苯基丙酸硫酯类化合物3a~3d;3a~3d在三氟乙酸(TFA)作用下脱除Boc保护基时,结果不仅得到了正常的脱保护基产物4a~4d,还生成了2-取代噻唑啉类化合物5a~5d,研究表明5a~5d是由4a~4d分子内脱水环合而成.通过优化三氟乙酸用量、反应温度以及反应时间等条件,能够以较高收率分别得到4a~4d和5a~5d(收率85%~91%和86%~89%).而S-[2-(叔丁氧羰基氨基)乙基]-3-苯基丙烯酸硫酯类化合物3e~3f由于双键结构,在三氟乙酸作用下仅生成脱除Boc保护基产物4e~4f.该反应的研究为2-取代噻唑啉类化合物的合成提供了一种简便有效的方法. S-2-(tert-Butoxycarbonylamino)ethyl 3-phenylpropanethioates (3a-3d) were synthesized in 79%-92% yields through the esterification of substituted 3-phenylpropanoic acids (1a-1d) and methyl N-(tert-butoxycarbonyl)-L-cysteine (2) by using bis(2-oxo-3-oxazolidinyl)phosphinic chloride (BOP-Cl) as the condensation agent. The deprotection of Boc group of 3a-3d by trifluoroacetic acid (TFA) gave not only normal deprotecting products 4a-4d but also 2-substituted thiazolines 5a-5d which were obtained by intramolecular dehydration of the corresponding 4a-4d, whereas the deprotection of Boc group of S-2-(tert-butoxycarbonylamino)ethyl 3-phenylpropenethioates (3e-3f) afforded only deprotecting products 4e-4f under the same condition due to their double bond rigid structures. 4a-4d and 5a-5d could be obtained in high yields (85%-91% and 86%-89%) respectively by optimizing reaction conditions on the amount of TFA, the reaction temperature and time, which provided a facile and effective method to synthesize 2-substituted thiazolines.
作者 贾尧玲 王洋
出处 《有机化学》 SCIE CAS CSCD 北大核心 2011年第4期538-543,共6页 Chinese Journal of Organic Chemistry
基金 国家自然科学基金(No.20972033) 国家新药重大专项课题(No.2009ZX09301-011) 中国科学院上海药物研究所新药研究国家重点实验室开放基金(No.SIMM1004KF-08)资助项目
关键词 S-[2-(叔丁氧羰基氨基)乙基]-3-苯基丙酸硫酯 噻唑啉 Boc保护基 三氟乙酸 S-2-(tert-butoxycarbonylamino)ethyl 3-phenylpropanethioate thiazoline Boc group trifluoroacetic acid (TFA)
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参考文献15

  • 1Veno, M.; Imaizumi, K.; Sugita, T.; Takata, I.; Takeshita, M. Int. J. Immunopharmacol. 1995, 17(7), 597.
  • 2Gerwick, W. H.; Proteau, P. J.; Nagle, D. G.; Hamel, E.; Blokhin, A.; Slate, D. J. Org. Chem. 1994, 59, 1243.
  • 3Li, H. Y.; Drummond, S.; Delucca, I.; Boswell, G. A. Tetrahedron 1996, 52(34), 11153.
  • 4毛杰,陈建宇,李如兴,王海英,李健,韩嘉祥.噻唑啉类化合物的合成和抑菌活性[J].应用化学,2004,21(12):1265-1268. 被引量:5
  • 5Xavier, F.; Elisabet, D.; Michel, L.; Fellous, R.; Lizzani-Cuvelier, L. Flavour Fragr. J. 2002, 17, 432.
  • 6Spencer, M.; Parliment, T.; Giordano, D. US 4355049,1982 [Chem. Abstr. 1982, 98, 52230].
  • 7Fu, B.; Du, D. M.; Xia, Q. Synthesis 2004, 221.
  • 8Vorbruggen, H.; Krolikiewicz, K. Tetrahedron 1993, 49, 9353.
  • 9Katritzky, A. R.; Cai, C. M.; Suzuki, K.; Singh, S. K. J. Org. Chem. 2004, 69, 811.
  • 10Aamer, S. Chin. Chem. Lett. 2009, 20, 1073.

二级参考文献5

  • 1Otto B,Wilhelm S. US 3 993 766[P],1976
  • 2Russell J B,Boyd L H. US 4 788 209[P],1988
  • 3Akinori H,Tomohiko E,Morifusa E, et al. Pest Manag Sci[J],2001,57:713
  • 4Xavier F,Elisabet D,Michel L, et al. Flavour Fragr J[J],2002,17:432
  • 5Gerhard S,Wuppertal-V. US 3 737 536[P],1973

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