[1]王玉琴.L-苯丙氨酸苄酯盐酸盐的合成新工艺研究[J].南京师范大学学报(工程技术版),2015,15(03):080.
 Wang Yuqin,Research on a New Techonology of Synthesis of L-PhenylalanineBenzyl Ester Hydrochloride[J].Journal of Nanjing Normal University(Engineering and Technology),2015,15(03):080.
点击复制

L-苯丙氨酸苄酯盐酸盐的合成新工艺研究
分享到:

南京师范大学学报(工程技术版)[ISSN:1006-6977/CN:61-1281/TN]

卷:
15卷
期数:
2015年03期
页码:
080
栏目:
化学工程
出版日期:
2015-09-20

文章信息/Info

Title:
Research on a New Techonology of Synthesis of L-PhenylalanineBenzyl Ester Hydrochloride
作者:
王玉琴12
(1.常州吉恩药业有限公司,江苏 常州 213127)
(2.江苏省多肽类及其衍生物医药工程技术研究中心,江苏 常州 213127)
Author(s):
Wang Yuqin12
(1.Genchem & Genpharm(Changzhou)
Co.,Ltd.,Changzhou 213127,China)
(Polypeptide Drug and Their Derivatives Engineering Research Center of Jiangsu Province,Changzhou 213127,China)
关键词:
L-苯丙氨酸苄酯盐酸盐L-苯丙氨酸合成
Keywords:
L-Phenylalanine benzyl ester hydrochlorideL-Phenylalaninesynthesis
分类号:
O625.5
文献标志码:
A
摘要:
提出了L-苯丙氨酸苄酯盐酸盐合成的新工艺路线,以L-苯丙氨酸为起始原料,先用二碳酸二叔丁酯保护氨基,再与氯化苄缩合得到N-叔丁氧羰基-L-苯丙氨酸苄酯,最后用氯化氢脱保护,得到L-苯丙氨酸苄酯盐酸盐. 通过实验探索了反应温度、原料配比、缚酸剂以及溶剂种类等工艺条件对合成的影响. 实验结果表明,在优化的工艺条件下,合成总收率为90.8%,为L-苯丙氨酸苄酯盐酸盐的合成提供了新选择.
Abstract:
The paper proposes a new technology line to synthesize L-Phenylalanine benzyl ester hydrochloride. L-Phenylalanine benzyl ester hydrochloride is synthesized from L-phenylalalanine via tert-butoxycarbonylation of amino with di-tert-butyl dicarbonate,condensation with benzyl chloride,and deprotection with hydrochloride solution in ethyl acetate. Through the experiments,the effects of such technology conditions as reaction temperatures,ingredients ratios,acid-binding agents and solvents on the synthesis are explored. The experimental results show that under the optimized techonological conditions,the overall yield of target product is 90.8%,and thus a new option is provided for the synthesis of L-Phenylalanine Benzyl Ester Hydrochloride.

参考文献/References:

[1]MillerHK,WaelschH.Benzylestersofaminoacids[J].JournaloftheAmericanChemicalSociety,1952,74:1092-1093.
[2]ErlangerBF,HallRM.Improvedsynthesisofaminoaicdbenzylesters[J].JournaloftheAmericanChemicalSociety,1954,76:5781-5782.
[3]PatelRP,PriceS.Synthesisofbenzylestersofα-aminoaicds[J].JournalofOrganicChemistry,1965,30:3575-3576.
[4]YoshioIwakura,KatsumiHayashi,SanamKang,etal.Benzylestersofα-aminoaicds[J].BulletinoftheChemicalSocietyofJapan,1964,37(11):1707-1709.
[5]LassenKM,LeeJ,JoulliéMM.SyntheticstudiesoftamandarinBsidechainanalogues[J].JournalofOrganicChemistry,2010,75(9):3027-3036.
[6]KellerO,KellerWE,LookGV,etal.Tert-Butoxycarbonylationofaminoacidsandtheirderivatives:N-tert-butoxycarbonyl-L-phenylalanine[J].OrganicSyntheses,1985,63:160.

备注/Memo

备注/Memo:
收稿日期:2015-01-07. 
通讯联系人:王玉琴,高级工程师,研究方向:有机物合成. E-mail:wyq@genchem.cn
更新日期/Last Update: 2015-09-20