KINETIC RESOLUTION OF PIPERAZINE-2-CARBOXAMIDE BY LEUCINE AMINOPEPTIDASE - AN APPLICATION IN THE SYNTHESIS OF THE NUCLEOSIDE TRANSPORT BLOCKER (-)DRAFLAZINE

被引：24

作者：

BRUCE, MA ^{[1
]}

LAURENT, DRS ^{[1
]}

POINDEXTER, GS ^{[1
]}

MONKOVIC, I ^{[1
]}

HUANG, S ^{[1
]}

BALASUBRAMANIAN, N ^{[1
]}

机构：

[1] BRISTOL MYERS SQUIBB CO,PHARMACEUT RES INST,WALLINGFORD,CT 06492

来源：

SYNTHETIC COMMUNICATIONS | 1995年 / 25卷 / 17期

关键词：

D O I：

10.1080/00397919508011814

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The resolution of N-t-Boc-piperazine carboxamide 5 proceeded smoothly in the presence of leucine aminopeptidase to produce acid (S)-1 and amide (R)-5 with good optical purity. Sequential alkylation and functional group manipulation of carboxamide (S)-5 provided the known nucleoside transport blocker draflazine (-) 2.

引用

页码：2673 / 2684

页数：12

共 19 条

[11] SYNTHESIS OF RACEMIC ALPHA-AMINO CARBOXAMIDES VIA LEWIS ACID-MEDIATED REACTIONS OF ALPHA-METHOXYGLYCINAMIDE DERIVATIVES WITH ALLYLSILANES - ENZYMATIC RESOLUTION TO OPTICALLY-ACTIVE ALPHA-AMINO-ACIDS [J].

ROOS, EC ;

MOOIWEER, HH ;

HIEMSTRA, H ;

SPECKAMP, WN ;

KAPTEIN, B ;

BOESTEN, WHJ ;

KAMPHUIS, J .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (25) :6769-6778

[12]

ROTEMAN R, 1977, Patent No. 4017513

[13] CHEMOENZYMATIC SYNTHESIS OF AMINO-ACIDS AND DERIVATIVES [J].

SCHOEMAKER, HE ;

BOESTEN, WHJ ;

KAPTEIN, B ;

HERMES, HFM ;

SONKE, T ;

BROXTERMAN, QB ;

VANDENTWEEL, WJJ ;

KAMPHUIS, J .

PURE AND APPLIED CHEMISTRY, 1992, 64 (08) :1171-1175

[14]

SMITH EL, 1955, METHOD ENZYMOL, V2, P88

[15] CATALYTIC ASYMMETRIC CONSTRUCTION OF MORPHOLINES AND PIPERAZINES BY PALLADIUM-CATALYZED TANDEM ALLYLIC SUBSTITUTION-REACTIONS [J].

UOZUMI, Y ;

TANAHASHI, A ;

HAYASHI, T .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (24) :6826-6832

[16]

VANBELLE H, 1993, CARDIOVASC RES, V27, P68

[17] COMPARATIVE PHARMACOLOGY OF NUCLEOSIDE TRANSPORT INHIBITORS [J].

VANBELLE, H ;

JANSSEN, PAJ .

NUCLEOSIDES & NUCLEOTIDES, 1991, 10 (05) :975-982

[18]

VANDAELE G, 1989, Patent No. 4766125

[19]

Williams R. M, 1989, SYNTHESIS OPTICALLY, P257

← 1 2 →