An improved synthesis of [24-14C]cholic acid, and its application to the synthesis of [14C]SCH 209702 (Syn3).: Synthesis of [2H8]SCH 209702

被引:3
作者
Ren, Sumei [1 ]
McNamara, Paw [1 ]
Kahairski, Davd [1 ]
机构
[1] Schering Plough Res Inst, Kenilworth, NJ 07033 USA
关键词
24-(14)C]cholic acid; bile acid; SCH; 209702; Syn3; carbon-14; synthesis;
D O I
10.1002/jlcr.1509
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
An efficient synthesis of [24- (14)C]cholic acid from potassium [(14)C]cyanide has been developed. The key intermediate, 23-chloro-3 alpha, 7 alpha, 12 alpha-triformyloxynorcholane, was synthesized by degradation of triformyl protected cholic acid. Different degradation conditions were explored. The synthesis of [(14)C]SCH 209702 from 23-chloro-3 alpha, 7 alpha, 12 alpha-triformyloxynorcholane and potassium [(14)C]cyanide is described. The synthesis of [(2)H(8)]SCH 209702 from [(2)H(4)]cholic acid is also presented.
引用
收藏
页码:231 / 235
页数:5
相关论文
共 15 条
[1]   THE PREPARATION OF SOME CARBOXYLABELLED BILE ACIDS - BILE ACIDS AND STEROIDS-2 [J].
BERGSTROM, S ;
ROTTENBERG, M ;
VOLTZ, J .
ACTA CHEMICA SCANDINAVICA, 1953, 7 (03) :481-484
[2]   LABELED BILE-ACIDS .2. METHYL 3-BETA-HYDROXYCHOL-5-EN-24-OATE, LABELED WITH C-13 AND OR H-2 [J].
BYON, CY ;
GUT, M ;
LAI, CK .
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1984, 21 (01) :65-73
[3]  
ENGLER H, 2004, Patent No. 2004108088
[4]  
ENGLER H, 2003, Patent No. 03053365
[5]  
ENGLER H, 2001, Patent No. 20010006946
[6]  
ENGLER H, 2005, Patent No. 20050025742
[7]   STEROID-SYNTHESIS - MODIFIED HUNSDIECKER DEGRADATION OF BILE-ACIDS AND RELATED COMPOUNDS [J].
KNAPP, FF .
STEROIDS, 1979, 33 (03) :245-249
[8]  
Kurti L., 2005, STRATEGIC APPL NAMED, P218
[9]   LABELED BILE-ACIDS .6. [22,23,24-13C3]-METHYL 3-ALPHA,7-ALPHA-DIACETOXY-5-BETA-CHOLAN-24-OATE, [22,23,24-C-13(3)]-METHYL 3-BETA-ACETOXYCHOL-5-EN-24-OATE, AND [16,17,22,23-4-3(4)]-METHYL 3-BETA-ACETOXYCHOL-5-EN-24-OATE [J].
LAI, CK ;
BYON, CY ;
ANDERSON, WG ;
GUT, M .
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1986, 23 (09) :957-961
[10]   LABELED BILE-ACIDS .4. BASE-CATALYZED ONE-POT SYNTHESIS OF DEUTERIUM LABELED BILE-ACIDS [J].
LAI, CK ;
BYON, CY ;
GUT, M ;
NAGAHISA, A .
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1984, 21 (07) :615-626