A convenient two-step one-pot synthesis of phosphonamidates

被引：11

作者：

Mlodnosky, KL ^{[1
]}

Holmes, HM ^{[1
]}

Lam, VQ ^{[1
]}

Berkman, CE ^{[1
]}

机构：

[1] SAN FRANCISCO STATE UNIV,DEPT CHEM & BIOCHEM,SAN FRANCISCO,CA 94132

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 51期

关键词：

D O I：

10.1016/S0040-4039(97)10421-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Phosphonamidates are formed in high yield from a one-pot sequential reaction of a phosphonyl dichloride with an alcohol and then an amine in the presence of catalytic 1H-tetrazole. Undesired disubstitution of the phoshphonyl dichloride by the alcohol or the amine is minimal due to the presence of tetrazole. (C) 1997 Elsevier Science Ltd.

引用

页码：8803 / 8806

页数：4

共 9 条

[1] EVALUATION OF INTRINSIC BINDING-ENERGY FROM A HYDROGEN-BONDING GROUP IN AN ENZYME-INHIBITOR [J].

BARTLETT, PA ;

MARLOWE, CK .

SCIENCE, 1987, 235 (4788) :569-571

[2] THE SYNTHESIS AND SERINE BETA-LACTAMASE INHIBITORY ACTIVITY OF SOME PHOSPHONAMIDATE ANALOGS OF DIPEPTIDES [J].

BATESON, JH ;

GASSON, BC ;

KHUSHI, T ;

NEALE, JE ;

PAYNE, DJ ;

TOLSON, DA ;

WALKER, G .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (14) :1667-1672

[3] Synthesis of an immunogenic template for the generation of catalytic antibodies for (-)-cocaine hydrolysis [J].

Berkman, CE ;

Underiner, GE ;

Cashman, JR .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16) :5686-5689

[4] SYNTHESIS OF STEREOCHEMICALLY DEFINED PHOSPHONAMIDATE-CONTAINING PEPTIDES - INHIBITORS FOR THE HIV-1 PROTEINASE [J].

CAMP, NP ;

HAWKINS, PCD ;

HITCHCOCK, PB ;

GANI, D .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1992, 2 (09) :1047-1052

[5]

GANDAS A, 1995, NUCLEOS NUCLEOT, V14, P825

[6] PHOSPHONAMIDATES AND PHOSPHONAMIDATE ESTERS AS HIV-1 PROTEASE INHIBITORS [J].

MCLEOD, DA ;

BRINKWORTH, RI ;

ASHLEY, JA ;

JANDA, KD ;

WIRSCHING, P .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1991, 1 (11) :653-+

[7] MECHANISM OF INHIBITION OF THE CLASS-C BETA-LACTAMASE OF ENTEROBACTER-CLOACAE P99 BY PHOSPHONATE MONOESTERS [J].

RAHIL, J ;

PRATT, RF .

BIOCHEMISTRY, 1992, 31 (25) :5869-5878

[8] Synthesis and pKa evaluation of model phosphonamidic, phosphonamidothioic, and phosphonamidodithioic acids [J].

Suarez, AI ;

Lin, J ;

Thompson, CM .

TETRAHEDRON, 1996, 52 (17) :6117-6124

[9] TETRAZOLE CATALYZED SYNTHESIS OF PHOSPHONATE ESTERS [J].

ZHAO, K ;

LANDRY, DW .

TETRAHEDRON, 1993, 49 (02) :363-368

← 1 →