Solventless Synthesis of N-Protected Amino Acids in a Ball Mill

被引:45
|
作者
Konnert, Laure [1 ]
Gauliard, Anne [1 ]
Lamaty, Frederic [1 ]
Martinez, Jean [1 ]
Colacino, Evelina [1 ]
机构
[1] Univ Montpellier 2, UMR CNRS UM 1 UM 2 5247, IBMM, F-34095 Montpellier 5, France
来源
关键词
Amino Acids; Ball mill; Protective groups; Solvent free; E-factor; NUCLEOSIDE; ANALOGS; ESTERS;
D O I
10.1021/sc4001115
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An eco-friendly methodology for preparing carbamate N-protected alpha-amino acids is described using ball-milling technology. Some beta-amino acids were also investigated in this study. This solvent-free methodology gave Boc-, Z-, and Fmoc-N-protected compounds in good to excellent yields with improved environmental impact compared to classical syntheses in solution. Different planetary ball mills were employed. The results are also discussed according to the different process parameters (grinding material, number of balls, rotation speed).
引用
收藏
页码:1186 / 1191
页数:6
相关论文
共 50 条
  • [1] Solventless Mechanosynthesis of N-Protected Amino Esters
    Konnert, Laure
    Lamaty, Frederic
    Martinez, Jean
    Colacino, Evelina
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (09): : 4008 - 4017
  • [2] SYNTHESIS OF ACTIVATED ESTERS OF N-PROTECTED AMINO-ACIDS
    WOLMAN, Y
    LADKANY, D
    FRANKEL, M
    [J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (08): : 689 - &
  • [3] USE OF ETHOXYACETYLENE FOR SYNTHESIS OF N-PROTECTED AMINO-ACIDS
    BANKS, GR
    COHEN, D
    PATTENDE.GE
    THOMAS, JAG
    [J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (02): : 126 - &
  • [4] Activation of carboxylic acids by pyrocarbonates: Synthesis of alkylamides of N-protected amino acids
    Pozdnev, VF
    [J]. BIOORGANICHESKAYA KHIMIYA, 1997, 23 (04): : 262 - 265
  • [5] Derivatives of aminoquinones with N-protected amino acids
    Chrysostomos Pachatouridis
    Elias A. Couladouros
    Vassilios P. Papageorgiou
    Maria Liakopoulou-Kyriakides
    [J]. Letters in Peptide Science, 1998, 5 (4): : 259 - 262
  • [6] Derivatives of Aminoquinones with N-protected Amino Acids
    Chrysostomos Pachatouridis
    Elias A. Couladouros
    Vassilios P. Papageorgiou
    Maria Liakopoulou-Kyriakides*
    [J]. Letters in Peptide Science, 1998, 5 (4): : 259 - 262
  • [7] Derivatives of aminoquinones with N-protected amino acids
    Pachatouridis, C
    Couladouros, EA
    Papageorgiou, VP
    Liakopoulou-Kyriakides, M
    [J]. LETTERS IN PEPTIDE SCIENCE, 1998, 5 (04): : 259 - 262
  • [8] A Facile Approach to the Synthesis of Benzothiazoles from N-Protected Amino Acids
    Arfan, M.
    Tahira, A.
    Mannan, A.
    Fatima, T.
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 56 (02) : 292 - 297
  • [9] A Facile Approach to the Synthesis of Benzothiazoles from N-Protected Amino Acids
    M. Arfan
    A. Tahira
    A. Mannan
    T. Fatima
    [J]. Russian Journal of Organic Chemistry, 2020, 56 : 292 - 297
  • [10] SYNTHESIS AND REACTIONS OF ESTERS OF N-HYDROXYPHTHALIMIDE AND N-PROTECTED AMINO ACIDS
    NEFKENS, GHL
    NIVARD, RJF
    TESSER, GI
    [J]. RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS-JOURNAL OF THE ROYAL NETHERLANDS CHEMICAL SOCIETY, 1962, 81 (08): : 683 - &