A PRACTICAL SYNTHESIS OF 5-(CHLOROMETHYL)FURO[2,3-B]PYRIDINE, A KEY INTERMEDIATE FOR THE HIV PROTEASE INHIBITOR, L-754,394

被引：36

作者：

BHUPATHY, M ^{[1
]}

CONLON, DA ^{[1
]}

WELLS, KM ^{[1
]}

NELSON, JR ^{[1
]}

REIDER, PJ ^{[1
]}

ROSSEN, K ^{[1
]}

SAGER, JW ^{[1
]}

VOLANTE, RP ^{[1
]}

DORSEY, BD ^{[1
]}

HOFFMAN, JM ^{[1
]}

JOSEPH, SA ^{[1
]}

MCDANIEL, SL ^{[1
]}

机构：

[1] MERCK SHARP & DOHME RES LABS,DEPT MED CHEM,W POINT,PA 19486

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1995年 / 32卷 / 04期

关键词：

D O I：

10.1002/jhet.5570320431

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical synthesis of 5-(chloromethyl)furo[2,3-b]pyridine (10), the side chain used to incorporate a key pharmacophore of the HIV protease inhibitor, L-754,394, is described. The synthesis was accomplished in ten steps and in 15% overall yield from commercially available methyl 2-furoate.

引用

页码：1283 / 1287

页数：5

共 10 条

[1] HIGHLY DIASTEREOSELECTIVE REACTION OF A CHIRAL, NON-RACEMIC AMIDE ENOLATE WITH (S)-GLYCIDYL TOSYLATE - SYNTHESIS OF THE ORALLY-ACTIVE HIV-1 PROTEASE INHIBITOR L-735,524
ASKIN, D
ENG, KK
ROSSEN, K
PURICK, RM
WELLS, KM
VOLANTE, RP
REIDER, PJ
[J]. TETRAHEDRON LETTERS, 1994, 35 (05) : 673 - 676
[2] COPPER-QUINOLINE DECARBOXYLATION
COHEN, T
SCHAMBACH, RA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (10) : 3189 - +
[3] L-735,524 - THE DESIGN OF A POTENT AND ORALLY BIOAVAILABLE HIV PROTEASE INHIBITOR
DORSEY, BD
LEVIN, RB
MCDANIEL, SL
VACCA, JP
GUARE, JP
DARKE, PL
ZUGAY, JA
EMINI, EA
SCHLEIF, WA
QUINTERO, JC
LIN, JH
CHEN, IW
HOLLOWAY, MK
FITZGERALD, PMD
AXEL, MG
OSTOVIC, D
ANDERSON, PS
HUFF, JR
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (21) : 3443 - 3451
[4] DORSEY BD, SYNTHESIS EVALUATION
[5] Freure BT., 1931, J AM CHEM SOC, V53, P1142
[6] FRIEDRICHSEN W, 1984, COMPREHENSIVE HETERO, V4, P974
[7] SYNTHESIS OF FUNCTIONALIZED FURO[2,3-B]PYRIDINES VIA THE PD-CATALYZED COUPLING OF ACETYLENES TO IODOPYRIDONES - PREPARATION OF A KEY INTERMEDIATE TO A NEW HIV PROTEASE INHIBITOR L-754,394
HOUPIS, IN
CHOI, WB
REIDER, PJ
MOLINA, A
CHURCHILL, H
LYNCH, J
VOLANTE, RP
[J]. TETRAHEDRON LETTERS, 1994, 35 (50) : 9355 - 9358
[8] NITRATION OF METHYL 2-FUROATE WITH ACETYL NITRATE - ON THE CONFIGURATIONS OF 6 ISOLATED INTERMEDIARY ADDUCTS
KOLB, VM
DARLING, SD
KOSTER, DF
MEYERS, CY
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (09) : 1636 - 1639
[9] A NEW SYNTHESIS OF FURO[2,3-B]PYRIDINE DERIVATIVES (1)
SNYDER, HR
EBETINO, FF
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1966, 3 (02) : 202 - &
[10] L-735,524 - AN ORALLY BIOAVAILABLE HUMAN-IMMUNODEFICIENCY-VIRUS TYPE-1 PROTEASE INHIBITOR
VACCA, JP
DORSEY, BD
SCHLEIF, WA
LEVIN, RB
MCDANIEL, SL
DARKE, PL
ZUGAY, J
QUINTERO, JC
BLAHY, OM
ROTH, E
SARDANA, VV
SCHLABACH, AJ
GRAHAM, PI
CONDRA, JH
GOTLIB, L
HOLLOWAY, MK
LIN, J
CHEN, IW
VASTAG, K
OSTOVIC, D
ANDERSON, PS
EMINI, EA
HUFF, JR
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1994, 91 (09) : 4096 - 4100

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