The synthesis of amides and dipeptides from unprotected amino acids by a simultaneous protection-activation strategy using boron trifluoride diethyl etherate

被引:13
作者
van Leeuwen, SH
Quaedflieg, PJLM
Broxterman, QB
Milhajlovic, Y
Liskamp, RMJ
机构
[1] Univ Utrecht, Utrecht Inst Pharmaceut Sci, Dept Med Chem, NL-3508 TB Utrecht, Netherlands
[2] DSM Res & Patents, Life Sci, Adv Synth, Catalysis & Dev, NL-6160 MD Geleen, Netherlands
关键词
amino acids; dipeptides; coupling; borontrifluoride etherate;
D O I
10.1016/j.tetlet.2004.11.129
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction Of L-phenylalanine (1) with boron trifluoride diethyl etherate and primary amines leads to the formation of amides via a cyclic boron intermediate. It is also possible to use the amino dicarboxylic acid L-aspartic acid and N-alkylated amino acids (peptoid building blocks, e.g., NPhe-OH 9). The latter can be used in the preparation of dipeptidomimetics. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:653 / 656
页数:4
相关论文
共 25 条
[1]  
BURGER K, 1990, CHEM ZTG, V114, P249
[2]   SYNTHESIS AND REACTIVITY OF BORON HETEROCYCLES DERIVED FROM AMINO-ACIDS [J].
DAS, MK ;
BANDYOPADHYAY, SN ;
ROY, S .
SYNTHESIS AND REACTIVITY IN INORGANIC AND METAL-ORGANIC CHEMISTRY, 1991, 21 (6-7) :931-939
[3]   Facile synthesis of block copolypeptides of defined architecture [J].
Deming, TJ .
NATURE, 1997, 390 (6658) :386-389
[4]   NMR-STUDIES OF 1,1-DIPHENYLBOROXAZOLIDONE DERIVATIVES OF ALPHA-AMINO-ACIDS [J].
FARFAN, N ;
SILVA, D ;
SANTILLAN, R .
HETEROATOM CHEMISTRY, 1993, 4 (06) :533-536
[5]   Boron complexes of L-cysteine [J].
González, A ;
Granell, J ;
Piniella, JF ;
Alvarez-Larena, A .
TETRAHEDRON, 1998, 54 (43) :13313-13322
[6]   STRUCTURE OF L-ALANINATODIPHENYLBORON [J].
GRAVELLE, PW ;
BOTT, SG .
JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 1995, 25 (08) :521-524
[7]  
HALSTROM J, 1978, J CHEM RES-S, P80
[8]   CONTROLLED SYNTHESIS OF PEPTIDES IN AQUEOUS MEDIUM .8. PREPARATION AND USE OF NOVEL ALPHA-AMINO ACID N-CARBOXYANHYDRIDES [J].
HIRSCHMANN, R ;
SCHWAM, H ;
STRACHAN, RG ;
SCHOENEWALDT, EF ;
BARKEMEYER, H ;
MILLER, SM ;
CONN, JB ;
GARSKY, V ;
VEBER, DF ;
DENKEWALTER, RG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (11) :2746-+
[9]   STEPWISE SYNTHESIS OF OLIGOPEPTIDES WITH N-CARBOXY-ALPHA AMINO ACID ANHYDRIDES .4. GLYCINE NCA [J].
KATAKAI, R ;
UNO, K ;
OYA, M ;
IWAKURA, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (02) :327-&
[10]  
KOSTER R, 1974, LIEBIGS ANN CHEM, P112