A comparison of catalysts to promote imidazolide couplings including the identification of 2-hydroxy-5-nitropyridine as a new, safe, and effective catalyst

被引：31

作者：

Dunn, PJ ^{[1
]}

Hoffmann, W

Kang, Y

Mitchell, JC

Snowden, MJ

机构：

[1] Pfizer Ltd, Global Res & Dev, Dept Chem Res & Dev, Sandwich CT13 9NJ, Kent, England

[2] Univ Greenwich, Chatham ME4 4TB, Kent, England

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2005年 / 9卷 / 06期

关键词：

D O I：

10.1021/op0580062

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Five catalysts were compared with respect to their safety and catalytic effectiveness for promoting imidazolide couplings, Reaction rate enhancement, shock sensitivity, and differential scanning calorimetry (DSC) data were considered in this analysis. 6-Chloro-1-hydroxybenzotriazole, which has been described in the literature as a safe catalyst, was found to be shock sensitive. 2-Hydroxy-5-nitropyridine is a new catalyst for this type of reaction and was found to be safe, effective, readily available, and similar in price to that of the 1-hydroxybenzotriazole, a common catalyst for promoting acylation reactions.

引用

页码：956 / 961

页数：6

共 15 条

[1] N,N'-CARBONYLDIIMIDAZOLE, A NEW REAGENT FOR PEPTIDE SYNTHESIS [J].

ANDERSON, GW ;

PAUL, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (16) :4423-4423

[2] Identification of new catalysts to promote imidazolide couplings and optimisation of reaction conditions using kinetic modelling [J].

Bright, R ;

Dale, DJ ;

Dunn, PJ ;

Hussain, F ;

Kang, Y ;

Mason, C ;

Mitchell, JC ;

Snowden, MJ .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2004, 8 (06) :1054-1058

[3]

CAREY JS, UNPUB ORG BIOMOL CHE

[4] The chemical development of the commercial route to sildenafil: A case history [J].

Dale, DJ ;

Dunn, PJ ;

Golightly, C ;

Hughes, ML ;

Levett, PC ;

Pearce, AK ;

Searle, PM ;

Ward, G ;

Wood, AS .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2000, 4 (01) :17-22

[5] The chemical development and scale-up of sampatrilat [J].

Dunn, PJ ;

Hughes, ML ;

Searle, PM ;

Wood, AS .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2003, 7 (03) :244-253

[6]

DUNN PJ, 2003, Patent No. 03080599

[7]

KOPPEL I, 1993, J CHEM RES-S, P446

[8] MOLECULAR REARRANGEMENTS .2. CLEAVAGE REACTIONS WITH BECKMANN REARRANGEMENT CONDITIONS [J].

LYLE, RE ;

LYLE, GG .

JOURNAL OF ORGANIC CHEMISTRY, 1953, 18 (08) :1058-1064

[9]

Marder O, 2003, CHIM OGGI, V21, P35

[10] FORMATION OF 1,2,3-TRIAZOLES, SECONDARY AMIDES, ALPHA-AMINOKETONES, AND VINYLKETONES IN ACID-CATALYZED DECOMPOSITION OF "5-HYDROXY-DELTA-2-1,2,3-TRIAZOLINES [J].

OLSEN, CE .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1975, 29 (09) :953-962

← 1 2 →