Polymer-assisted solution phase synthesis: a general method for sequestration of byproducts formed from activated acyl-transfer reactants

被引：38

作者：

Weidner, JJ ^{[1
]}

Parlow, JJ ^{[1
]}

Flynn, DL ^{[1
]}

机构：

[1] Monsanto Co, Parallel Med & Combinatorial Chem, Searle Discovery Res U2D, St Louis, MO 63167 USA

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 02期

关键词：

combinatorial chemistry; resins;

D O I：

10.1016/S0040-4039(98)02328-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Typical amide bond-forming reactions involving amines with activated esters are purified by the use of complementary molecular reactivity/molecular recognition (CMR/R) resins, which sequester both the excess activated ester and the byproducts (leaving group) generated. It is also shown by HPLC analysis that this strategy effectively removes many of the common byproducts generated from reactions involving activated esters, carbonates, and carbamates. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：239 / 242

页数：4

共 13 条

[1] Polymer-supported quenching reagents for parallel purification [J].

Booth, RJ ;

Hodges, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (21) :4882-4886

[2]

CARDILLO G, 1981, SYNTHESIS-STUTTGART, P793

[3]

CAREY FA, 1983, ADV ORG CHEM, P121

[4] Novel solution phase strategy for the synthesis of chemical libraries containing small organic molecules [J].

Cheng, S ;

Comer, DD ;

Williams, JP ;

Myers, PL ;

Boger, DL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (11) :2567-2573

[5]

Chucholowski A, 1996, CHIMIA, V50, P525

[6] Chemical library purification strategies based on principles of complementary molecular reactivity and molecular recognition [J].

Flynn, DL ;

Crich, JZ ;

Devraj, RV ;

Hockerman, SL ;

Parlow, JJ ;

South, MS ;

Woodard, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (21) :4874-4881

[7] Ion-exchange resins for solution phase parallel synthesis of chemical libraries [J].

Gayo, LM ;

Suto, MJ .

TETRAHEDRON LETTERS, 1997, 38 (04) :513-516

[8] Use of solid supported nucleophiles and electrophiles for the purification of non-peptide small molecule libraries [J].

Kaldor, SW ;

Siegel, MG ;

Fritz, JE ;

Dressman, BA ;

Hahn, PJ .

TETRAHEDRON LETTERS, 1996, 37 (40) :7193-7196

[9]

Lawrence RM, 1997, SYNTHESIS-STUTTGART, P553

[10] Utility of complementary molecular reactivity and molecular recognition (CMR/R) technology and polymer-supported reagents in the solution-phase synthesis of heterocyclic carboxamides [J].

Parlow, JJ ;

Mischke, DA ;

Woodard, SS .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17) :5908-5919

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