(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
  • [1] 2-[(tert-Butoxycarbonylamino)oxy]acetic acid
    Zhang, Jing-Yu
    Tong, Yan
    Wang, Shengqi
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O2324 - U153
  • [2] Ethyl 2-(tert-butoxycarbonylamino)-1,3-benzothiazole-6-carboxylate
    Lei, Can
    Fang, Xin
    Yu, Hai-Yang
    Huang, Ming-Dong
    Wang, Jun-Dong
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O914 - U3003
  • [3] 2-(tert-Butoxycarbonylamino)-2-(2-fluorophenyl)acetic acid
    Anwar, Muhammad Mahmood
    Iqbal, Muhammad Saeed
    Tahir, M. Nawaz
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O2891 - U2108
  • [4] Study on the Deprotection of Boc Group of S-2-(tert-Butoxycarbonylamino)ethyl 3-Phenylpropanethioates
    Jia, Yaoling
    Wang, Yang
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2011, 31 (04) : 538 - 543
  • [5] (2S)-Methyl 1-[(2R)-3-(benzylsulfanyl)-2-(tert-butoxycarbonylamino)propanoyl]pyrrolidine-2-carboxylate
    Raisanen, Minna T.
    Klinga, Martti
    Leskela, Markku
    Repo, Timo
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2007, 63 : O2095 - O2096
  • [6] (S)-O-succinimidyl N-[2-(tert-butoxycarbonylamino)propyl]carbamate
    Menschise, V
    Didierjean, C
    Semetey, V
    Guichard, G
    Briand, JP
    Aubry, A
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2001, 57 : o222 - o224
  • [7] Synthesis and Crystal Structure of S-ethyl-2(tert-butoxycarbonylamino)4-methyl-pentanethioate
    Dinesh, B.
    Manjunath, H. R.
    Naveen, S.
    Abiraj, K.
    Baba, A. Ramesh
    Gowda, D. Channe
    Sridhar, M. A.
    Prasad, J. Shashidhara
    MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 2010, 517 : 161 - 166
  • [8] Benzyl 2-{[2-(tert-butoxycarbonylamino)-4-methylpentanoyl]methylamino}-4-methylpentanoate
    Liao, Xiao-Jian
    Xu, Wen-Jie
    Xu, Shi-Hai
    Dong, Fang-Fang
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2007, 63 : O3313 - U4398
  • [9] Methyl 2-[2-(tert-butoxycarbonylamino)-1,3-benzothiazole-6-carboxamido]acetate
    Gao, Dan
    Fang, Xing
    Yu, Hai-Yang
    Wang, Jun-Dong
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2012, 68
  • [10] (Z)-N-[(2R,3R)-2-(TERT-BUTOXYCARBONYLAMINO)-3-(TERT-BUTYLDIPHENYLSILOXY)BUTYLIDENE]BENZYLAMINE N-OXIDE
    MERINO, P
    MERCHAN, FL
    TEJERO, T
    LANASPA, A
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1995, 51 (pt 9) : 1949 - 1950
12345