Catalyst and solvent-free amidation of inactive esters of N-protected amino acids

被引：20
|
作者：
Nadimpally, Krishna Chaitanya [1 ]
Thalluri, Kishore [1 ]
Palakurthy, Nani Babu [1 ]
Saha, Abhijit [1 ]
Mandal, Bhubaneswar [1 ]
机构：
[1] Indian Inst Technol, Dept Chem, Gauhati 781039, Assam, India
来源：
TETRAHEDRON LETTERS | 2011年 / 52卷 / 20期
关键词：
Aminolysis; Inactive esters; Amino acid; Amidation; MICROWAVE IRRADIATION; PEPTIDE SYNTHESIS; L-PHENYLALANINE; ACTIVE ESTERS; AMIDES; AMMONOLYSIS; DERIVATIVES;
D O I：
10.1016/j.tetlet.2011.03.039
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A catalyst free procedure for the preparation of amides from inactive esters of N-protected amino acids and various amines is demonstrated under mild reaction conditions. Our effort to recover excess amine and generated alcohol is an approach towards environment friendly and cost effective synthesis under easy operational conditions. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2579 / 2582
页数：4
相关论文
共 50 条
  • [1] SYNTHESIS OF ACTIVATED ESTERS OF N-PROTECTED AMINO-ACIDS
    WOLMAN, Y
    LADKANY, D
    FRANKEL, M
    JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (08): : 689 - &
  • [2] Peptide Mechanosynthesis by Direct Coupling of N-Protected -Amino Acids with Amino Esters
    Porte, Vincent
    Thioloy, Marion
    Pigoux, Titouan
    Metro, Thomas-Xavier
    Martinez, Jean
    Lamaty, Frederic
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (21) : 3505 - 3508
  • [3] P-CHLOROTETRAFLUOROPHENYL ESTERS OF N-PROTECTED AMINO-ACIDS
    MEDVEDKIN, VN
    KLIMENKO, LN
    MITIN, YV
    KRETSINGER, RH
    SHABANOWITZ, J
    ZABOLOTSKIKH, VF
    PODGORNOVA, NN
    INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH, 1994, 44 (05): : 477 - 484
  • [4] Salicylanilide esters of N-protected amino acids as novel antimicrobial agents
    Imramovsky, Ales
    Vinsova, Jarmila
    Ferriz, Juana Monreal
    Buchta, Vladimir
    Jampilek, Josef
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (02) : 348 - 351
  • [5] SYNTHESIS AND REACTIONS OF ESTERS OF N-HYDROXYPHTHALIMIDE AND N-PROTECTED AMINO ACIDS
    NEFKENS, GHL
    NIVARD, RJF
    TESSER, GI
    RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS-JOURNAL OF THE ROYAL NETHERLANDS CHEMICAL SOCIETY, 1962, 81 (08): : 683 - &
  • [6] Solventless Mechanosynthesis of N-Protected Amino Esters
    Konnert, Laure
    Lamaty, Frederic
    Martinez, Jean
    Colacino, Evelina
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (09): : 4008 - 4017
  • [7] Solvent-free biocatalytic amidation of carboxylic acids
    Prasad, AK
    Husain, M
    Singh, BK
    Gupta, RK
    Manchanda, VK
    Olsen, CE
    Parmar, VS
    TETRAHEDRON LETTERS, 2005, 46 (26) : 4511 - 4514
  • [8] INVESTIGATION ON RACEMIZATION OF ORTHO METHOXYPHENYL ESTERS OF N-PROTECTED AMINO-ACIDS
    BANKOWSKI, K
    DRABAREK, S
    ROCZNIKI CHEMII, 1972, 46 (04): : 607 - +
  • [9] A SIMPLE METHOD FOR THE PREPARATION OF DIPHENYLMETHYL ESTERS OF N-PROTECTED AMINO-ACIDS
    LAPATSANIS, L
    MILIAS, G
    PARASKEWAS, S
    SYNTHESIS-STUTTGART, 1985, (05): : 513 - 515
  • [10] Biocatalytic production of unnatural amino acids, mono esters and N-protected derivatives
    Fotheringham, IG
    Pantaleone, DP
    Taylor, PP
    CHIMICA OGGI-CHEMISTRY TODAY, 1997, 15 (9-10) : 33 - 37
12345