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Titolo:
PREPARATION OF OPTICALLY-ACTIVE SUCCINIC ACID-DERIVATIVES .1. OPTICALRESOLUTION OF -3-(CIS-HEXAHYDROISOINDOLIN-2-YLCARBONYL)PROPIONIC ACID
Autore:
YAMAGUCHI T; YANAGI T; HOKARI H; MUKAIYAMA Y; KAMIJO T; YAMAMOTO I;
Indirizzi:
KISSEI PHARMACEUT CO LTD,CENT RES LABS,4365-1 KASHIWABARA NAGANO 39983 JAPAN KISSEI PHARMACEUT CO LTD,CENT RES LABS NAGANO 39983 JAPAN SHINSHU UNIV UEDA NAGANO 386 JAPAN
Titolo Testata:
Chemical and Pharmaceutical Bulletin
fascicolo: 9, volume: 45, anno: 1997,
pagine: 1518 - 1520
SICI:
0009-2363(1997)45:9<1518:POOSA.>2.0.ZU;2-1
Fonte:
ISI
Lingua:
ENG
Soggetto:
SULFONYLUREA HYPOGLYCEMIC AGENT; DIABETES-MELLITUS RATS; RENIN INHIBITORS; DIHYDRATE KAD-1229; AMINO-ACID;
Keywords:
KAD-1229; POTENT HYPOGLYCEMIC EFFECT; OPTICAL RESOLUTION; 3-(CIS-HEXAHYDROISOINDOLIN-2-YL-CARBONYL)PROPIONIC ACID;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Science Citation Index Expanded
Citazioni:
14
Recensione:
Indirizzi per estratti:
Citazione:
T. Yamaguchi et al., "PREPARATION OF OPTICALLY-ACTIVE SUCCINIC ACID-DERIVATIVES .1. OPTICALRESOLUTION OF -3-(CIS-HEXAHYDROISOINDOLIN-2-YLCARBONYL)PROPIONIC ACID", Chemical and Pharmaceutical Bulletin, 45(9), 1997, pp. 1518-1520

Abstract

(+)-Monocalcium 3-(cis-hexahydroisindolin-2-ylcarbonyl)propionate] dihydrate (KAD-1229, 1) is an optically active succinic acid calcium salt derivative with potent hypoglycemic effect, We investigated two optical resolution methods, -3-(cis-hexahydroisoindolin-2-ylcarbonyl)propionic acid 6 was esterified with (S)-N-benzyl mandelamide and the resulting diastereomeric esters were separated by column chromatography on silica gel to give 7 and 8 in 39.1% and 45.3% yields, respectively. The diastereomer 7 was hydrolyzed to give the optically active acid (-)-6, The absolute configuration of(-)-6 was established as S by comparison with an authentic sample, The alternative method was resolution using an optically active amine, Treatment of a solution of the racemic acid 6 with 0.65eq of (R)-1-(1-naphthyl)ethylamine in ethanol gave the salt in 23.2% yield with an optical purity of 96.8% ee.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 23/11/20 alle ore 21:30:11