A practical method for the preparation of alpha'-chloroketones of N-carbamate protected-alpha-aminoacids

被引:49
作者
Chen, P
Cheng, PTW
Spergel, SH
Zahler, R
Wang, XB
Thottathil, J
Barrish, JC
Polniaszek, RP
机构
[1] BRISTOL MYERS SQUIBB PHARMACEUT RES INST,DISCOVERY CHEM,PRINCETON,NJ 08543
[2] CHEM PROC RES,NEW BRUNSWICK,NJ 08903
关键词
D O I
10.1016/S0040-4039(97)00605-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A practical method for the preparation of alpha-N-BOC-epoxides from protected amino acid esters based on the Kowalski homologation reaction is described This procedure can be readily performed on a large scale without the use of hazardous reagents and has allowed preparation of epoxides 3 in multi-kilogram quantities. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:3175 / 3178
页数:4
相关论文
共 22 条
[1]   STEREOCONTROLLED SYNTHESIS OF ERYTHRO N-PROTECTED ALPHA-AMINO EPOXIDES AND PEPTIDYL EPOXIDES [J].
ALBECK, A ;
PERSKY, R .
TETRAHEDRON, 1994, 50 (21) :6333-6346
[2]   HIGHLY DIASTEREOSELECTIVE ALKYLATIONS OF CHIRAL AMIDE ENOLATES - NEW ROUTES TO HYDROXYETHYLENE DIPEPTIDE ISOSTERE INHIBITORS OF HIV-1 PROTEASE [J].
ASKIN, D ;
WALLACE, MA ;
VACCA, JP ;
REAMER, RA ;
VOLANTE, RP ;
SHINKAI, I .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (10) :2771-2773
[3]   THE FIRST DIRECT PREPARATION OF CHIRAL FUNCTIONALIZED KETONES AND THEIR SYNTHETIC USES [J].
BARLUENGA, J ;
BARAGANA, B ;
ALONSO, A ;
CONCELLON, JM .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (08) :969-970
[4]   AMINODIOL HIV PROTEASE INHIBITORS .1. DESIGN, SYNTHESIS, AND PRELIMINARY SAR [J].
BARRISH, JC ;
GORDON, E ;
ALAM, M ;
LIN, PF ;
BISACCHI, GS ;
CHEN, P ;
CHENG, PTW ;
FRITZ, AW ;
GREYTOK, JA ;
HERMSMEIER, MA ;
HUMPHREYS, WG ;
LIS, KA ;
MARELLA, MA ;
MERCHANT, Z ;
MITT, T ;
MORRISON, RA ;
OBERMEIER, MT ;
PLUSCEC, J ;
SKOOG, M ;
SLUSARCHYK, WA ;
SPERGEL, SH ;
STEVENSON, JM ;
SUN, CQ ;
SUNDEEN, JE ;
TAUNK, P ;
TINO, JA ;
WARRACK, BM ;
COLONNO, RJ ;
ZAHLER, R .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (12) :1758-1768
[5]   LARGE-SCALE PREPARATION OF (2S,3S)-N-BOC-3-AMINO-1,2-EPOXY-4-PHENYLBUTANE - A KEY BUILDING-BLOCK FOR HIV-PROTEASE INHIBITORS [J].
BEAULIEU, PL ;
WERNIC, D ;
DUCEPPE, JS ;
GUINDON, Y .
TETRAHEDRON LETTERS, 1995, 36 (19) :3317-3320
[6]   ALPHA-AMINO-ACIDS AS CHIRAL EDUCTS FOR ASYMMETRIC PRODUCTS - AMINO ACYLATION WITH N-ACYLAMINO ACIDS [J].
BUCKLEY, TF ;
RAPOPORT, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (20) :6157-6163
[7]  
CHEN P, 1996, Patent No. 5481011
[8]   A STEREOCONTROLLED SYNTHESIS OF HYDROXYETHYLENE DIPEPTIDE ISOSTERES USING NOVEL, CHIRAL AMINOALKYL EPOXIDES AND GAMMA-(AMINOALKYL) GAMMA-LACTONES [J].
EVANS, BE ;
RITTLE, KE ;
HOMNICK, CF ;
SPRINGER, JP ;
HIRSHFIELD, J ;
VEBER, DF .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (23) :4615-4625
[9]   DESIGN OF PEPTIDE DERIVED AMINO-ALCOHOLS AS TRANSITION-STATE ANALOG INHIBITORS OF ANGIOTENSIN CONVERTING ENZYME [J].
GORDON, EM ;
GODFREY, JD ;
PLUSCEC, J ;
VONLANGEN, D ;
NATARAJAN, S .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1985, 126 (01) :419-426
[10]  
GREEN BE, 1995, SYNLETT, P613