An improved synthesis of N-aryl-hydantoin LFA-1 antagonists via the enantiospecific alkylation of an isobutyraldehyde-derived imidazolidinone template

被引:27
作者
Frutos, RP [1 ]
Stehle, S [1 ]
Nummy, L [1 ]
Yee, N [1 ]
机构
[1] Boehringer Ingelheim Pharmaceut Inc, Dept Chem Dev, Ridgefield, CT 06877 USA
关键词
D O I
10.1016/S0957-4166(01)00009-X
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
An improved and cost-effective process for the synthesis of N-aryl-hydantoin LFA-1 antagonists is described. Key transformations include the synthesis and stereospecific alkylation of the trans-isobutyraldehyde-derived template 4, and the one-pot hydrolysis of intermediate 6. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:101 / 104
页数:4
相关论文
共 10 条
[1]   Stereoselective synthesis of quaternary α-amino acids.: Part 1:: Acyclic compounds [J].
Cativiela, C ;
Diaz-de-Villegas, MD .
TETRAHEDRON-ASYMMETRY, 1998, 9 (20) :3517-3599
[2]   Synthesis of protected, chiral α,α-disubstituted α-amino acids via a Beckmann rearrangement [J].
Frutos, RP ;
Spero, DM .
TETRAHEDRON LETTERS, 1998, 39 (17) :2475-2478
[3]   BASE-PROMOTED HYDROLYSIS OF AMIDES AT AMBIENT-TEMPERATURES [J].
GASSMAN, PG ;
HODGSON, PKG ;
BALCHUNIS, RJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (05) :1275-1276
[4]   HIGHLY DIASTEREOSELECTIVE ALKYLATION OF 1-BENZOYL-2-ALKYL-3-(1'-METHYLBENZYL)IMIDAZOLIDIN-4-ONES [J].
JUARISTI, E ;
ANZORENA, JL ;
BOOG, A ;
MADRIGAL, D ;
SEEBACH, D ;
GARCIABAEZ, EV ;
GARCIABARRADAS, O ;
GORDILLO, B ;
KRAMER, K ;
STEINER, I ;
ZURCHER, S .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (20) :6408-6415
[5]  
Kelly TA, 1999, J IMMUNOL, V163, P5173
[6]   SYNTHESIS AND N-METHYL-D-ASPARTATE (NMDA) ANTAGONIST PROPERTIES OF THE ENANTIOMERS OF ALPHA-AMINO-5-(PHOSPHONOMETHYL)[1,1'-BIPHENYL]-3-PROPANOIC ACID - USE OF A NEW CHIRAL GLYCINE DERIVATIVE [J].
MULLER, W ;
LOWE, DA ;
NEIJT, H ;
URWYLER, S ;
HERRLING, PL ;
BLASER, D ;
SEEBACH, D .
HELVETICA CHIMICA ACTA, 1992, 75 (03) :855-864
[7]   ADDITION OF CHIRAL GLYCINE, METHIONINE, AND VINYLGLYCINE ENOLATE DERIVATIVES TO ALDEHYDES AND KETONES IN THE PREPARATION OF ENANTIOMERICALLY PURE ALPHA-AMINO-BETA-HYDROXY ACIDS [J].
SEEBACH, D ;
JUARISTI, E ;
MILLER, DD ;
SCHICKLI, C ;
WEBER, T .
HELVETICA CHIMICA ACTA, 1987, 70 (01) :237-261
[8]  
SEEBACH D, 1996, ANGEW CHEM INT EDIT, V35, P2709
[9]   Enantioselective synthesis of alpha,alpha-disubstituted amino acid derivatives via enzymatic resolution: Preparation of a thiazolyl-substituted alpha-methyl alpha-benzyl amine [J].
Spero, DM ;
Kapadia, SR .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (21) :7398-7401
[10]   Self-regeneration of stereocenters: A practical enantiospecific synthesis of LFA-1 antagonist BIRT-377 [J].
Yee, NK .
ORGANIC LETTERS, 2000, 2 (18) :2781-2783