(S)-Ethyl 2-(tert-butoxycarbonylamino)-3-(2-iodo-4,5-methylenedioxyphenyl)propanoate

被引：0
|
作者：
Lentini, Giovanni [1 ]
Cavalluzzi, Maria Maddalena [1 ]
Degennaro, Leonardo [1 ]
Fracchiolla, Giuseppe [1 ]
Perna, Filippo [1 ]
Scilimati, Antonio [1 ]
机构：
[1] Univ Bari, Dept Pharm Pharmaceut Sci, Via E Orabona 4, I-70126 Bari, Italy
来源：
MOLBANK | 2019年 / 01期
关键词：
phenylalanine; l-DOPA; iodination; medicinal chemistry; FLUORINATION; F-18;
D O I：
10.3390/M1049
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A multistep gram-scale synthesis of (S)-ethyl 2-(tert-butoxycarbonylamino)-3-(2-iodo-4,5-methylenedioxyphenyl)propanoate (2) has been developed. The title compound was prepared starting from commercially available l-DOPA which was O- and N-protected before undergoing iodination by CF3CO2Ag/I-2. The structure of the target compound was confirmed using IR, H-1-NMR, C-13-NMR, 2D (COSY, HSQC) NMR spectroscopy, as well as ESI-MS and HRMS.
引用
收藏
页数：4
相关论文
共 50 条
  • [31] A Spectroscopic and Diffractometric Study of Polymorphism in Ethyl 3-{3-[((2R)-3-{[2-(2,3-dihydro-1H-inden-2-yl)-1,1-dimethylethyl]amino}-2-hydroxypropyl)oxy]-4,5-difluorophenyl}propanoate Hydrochloride
    Vogt, Frederick G.
    Williams, Glenn R.
    Johnson, Matthew N.
    Copley, Royston C. B.
    CRYSTAL GROWTH & DESIGN, 2013, 13 (12) : 5353 - 5367
  • [32] Enantioselective Synthesis of Benzyl (1S,2R,4R)-4-(tert-Butoxycarbonylamino)-2-(hydroxymethyl)cyclohexylcarbamate Using an Iodolactamization As the Key Step
    Campbell, Carlton L.
    Hassler, Carla
    Ko, Soo S.
    Voss, Matthew E.
    Guaciaro, Michael A.
    Carter, Percy H.
    Cherney, Robert J.
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (16): : 6368 - 6370
  • [33] PREPARATION AND BIODISTRIBUTION OF 1-[2-(3-[I-125]IODO-4-AMINOPHENYL)ETHYL]-4-[3-(TRIFLUOROMETHYL)PHENYL]PIPERAZINE AND 1-[2-(3-[I-125]IODO-4-AZIDOPHENYL)ETHYL]-4-[3-(TRIFLUOROMETHYL)PHENYL]PIPERAZINE
    CHUMPRADIT, S
    KUNG, HF
    BILLINGS, J
    GUO, YZ
    WU, Y
    SHIH, J
    JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (03) : 543 - 547
  • [34] Crystal structure of 2-ethyl-1-tert-butyl-2-((4-fluorophenyl)(tert-butoxycarbonylamino)methyl)-3-oxo-pyrrolidine-1,2-dicarboxylate, C24H33FN2O7
    Makhathini, Sifiso S.
    Samipillai, Marivel
    Govender, Thavendran
    Naicker, Tricia
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2016, 231 (03): : 819 - 821
  • [35] Analysis of 1-(3-methoxy-4,5-methylenedioxyphenyl)-2-propanamine (MMDA) derivatives synthesized from Nutmeg oil and 3-methoxy-4,5-methylenedioxybenzaldehyde
    J Chromatogr Sci, 1 (34):
  • [36] 2-(tert-Butoxycarbonylamino)-6-(1,3-dioxo-1H-2,3-dihydrobenzo[de]isoquinolin-2-yl)hexanoic acid
    Fun, Hoong-Kun
    Goh, Jia Hao
    Qiu, Zhenjun
    Zhang, Yan
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O1198 - U1123
  • [37] SYNTHESIS OF ETHYL 2-[4-(3-FLUORO-2-QUINOXALINYLOXY)PHENOXY]PROPANOATE AS HERBICIDE
    MAKINO, K
    YOSHIOKA, H
    JOURNAL OF FLUORINE CHEMISTRY, 1987, 37 (01) : 119 - 124
  • [38] 3-[2-(3-Chlorophenyl)ethyl]pyridine-2-carbonitrile
    Li, XP
    Chen, HY
    Wang, XM
    Zhou, CX
    Zhao, Y
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2005, 61 : O1810 - O1811
  • [39] Analysis of 1-(3-methoxy-4,5-methylenedioxyphenyl)-2-propanamine (MMDA) derivatives synthesized from nutmeg oil and 3-methoxy-4,5-methylenedioxybenzaldehyde
    Clark, CR
    DeRuiter, J
    Noggle, FT
    JOURNAL OF CHROMATOGRAPHIC SCIENCE, 1996, 34 (01) : 34 - 42
  • [40] PSILOCIN ANALOGS .2. SYNTHESIS OF 3-[2-(DIALKYLAMINO)ETHYL]-4-OLS, 3-[2-(N-METHYL-N-ALKYLAMINO)ETHYL]-4-OLS, AND 3-[2-(CYCLOALKYLAMINO)ETHYL]INDOL-4-OLS
    REPKE, DB
    FERGUSON, WJ
    BATES, DK
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1981, 18 (01) : 175 - 179
12345