Synthesis of 3H, 14C and 13C6 labelled Sch 58235

被引：10

作者：

Hesk, D ^{[1
]}

Bignan, G ^{[1
]}

Lee, J ^{[1
]}

Yang, J ^{[1
]}

Voronin, K ^{[1
]}

Magatti, C ^{[1
]}

McNamara, P ^{[1
]}

Koharski, D ^{[1
]}

Hendershot, S ^{[1
]}

Saluja, S ^{[1
]}

Wang, S ^{[1
]}

机构：

[1] Schering Plough Corp, Res Inst, Kenilworth, NJ 07033 USA

来源：

JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS | 2002年 / 45卷 / 02期

关键词：

Sch; 58235; tritium; carbon-13; carbon-14; synthesis;

D O I：

10.1002/jlcr.539

中图分类号：

Q5 [生物化学];

学科分类号：

071010 ; 081704 ;

摘要：

H-3-Sch 58235 was prepared at a specific activity of 29.1 Ci/mmol by Ir(COD)(CY3P)PyPF6 catalysed exchange with tritium gas. C-14-Sch 58235 was prepared in three steps from p-hydroxy[ring-U-C-14]benzaldehyde with an overall radiochemical yield of 21%. C-13(6)-Sch 58235 was similarly prepared in three steps from p-hydroxy[ring-U-C-13(6)]benzaldehyde in an overall yield of 41%. Copyright (C) 2002 John Wiley Sons, Ltd.

引用

页码：145 / 155

页数：11

共 9 条

[1] 2-AZETIDINONES AS INHIBITORS OF CHOLESTEROL ABSORPTION
BURNETT, DA
CAPLEN, MA
DAVIS, HR
BURRIER, RE
CLADER, JW
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (12) : 1733 - 1736
[2] 2-azetidinone cholesterol absorption inhibitors: Structure-activity relationships on the heterocyclic nucleus
Clader, JW
Burnett, DA
Caplen, MA
Domalski, MS
Dugar, S
Vaccaro, W
Sher, R
Browne, ME
Zhao, HR
Burrier, RE
Salisbury, B
Davis, HR
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (19) : 3684 - 3693
[3] HIGHLY ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES - MECHANISM AND SYNTHETIC IMPLICATIONS
COREY, EJ
BAKSHI, RK
SHIBATA, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) : 5551 - 5553
[4] IRIDIUM COMPOUNDS IN CATALYSIS
CRABTREE, R
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1979, 12 (09) : 331 - 338
[5] DEUTERATION OF ACETANILIDES AND OTHER SUBSTITUTED AROMATICS USING [IR(COD)(CY(3)P)(PY)]PF6 AS CATALYST
HESK, D
DAS, PR
EVANS, B
[J]. JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1995, 36 (05) : 497 - 502
[6] HESK D, 1979, J LAB COMPOUNDS RADI, V38, P1039
[7] AN ASYMMETRIC-SYNTHESIS OF MK-0417 - OBSERVATIONS ON OXAZABOROLIDINE-CATALYZED REDUCTIONS
JONES, TK
MOHAN, JJ
XAVIER, LC
BLACKLOCK, TJ
MATHRE, DJ
SOHAR, P
JONES, ETT
REAMER, RA
ROBERTS, FE
GRABOWSKI, EJJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) : 763 - 769
[8] Discovery of 1-(4-fluorophenyl)-(3R)-[3-(4-fluorophenyl)-(3S)-hydroxypropyl]-(4S)-(4-hydroxyphenyl)-2-azetidinone (SCH 58235):: A designed, potent, orally active inhibitor of cholesterol absorption
Rosenblum, SB
Huynh, T
Afonso, A
Davis, HR
Yumibe, N
Clader, JW
Burnett, DA
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (06) : 973 - 980
[9] Organoiridium catalyzed hydrogen isotope exchange: Ligand effects on catalyst activity and regioselectivity
Shu, AYL
Chen, W
Heys, JR
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1996, 524 (1-2) : 87 - 93

← 1 →