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Titolo:
PREPARATION OF OPTICALLY-ACTIVE SUCCINIC ACID-DERIVATIVES - III - REGIOSELECTIVE CONDENSATION-REACTIONS OF OPTICALLY-ACTIVE 2-SUBSTITUTED SUCCINIC ACIDS WITH DIIMIDAZOLIDE
Autore:
YAMAGUCHI T; YANAGI T; HOKARI H; MUKAIYAMA Y; KAMIJO T; YAMAMOTO I;
Indirizzi:
KISSEI PHARMAEUT CO LTD,CENT RES LABS,4365-1 KASHIWABARA NAGANO 3998304 JAPAN KISSEI PHARMAEUT CO LTD,CENT RES LABS NAGANO 3998304 JAPAN SHINSHU UNIV NAGANO 3868567 JAPAN
Titolo Testata:
Yakugaku zasshi
fascicolo: 6, volume: 118, anno: 1998,
pagine: 248 - 255
SICI:
0031-6903(1998)118:6<248:POOSA->2.0.ZU;2-C
Fonte:
ISI
Lingua:
JPN
Soggetto:
SULFONYLUREA HYPOGLYCEMIC AGENT; DIABETES-MELLITUS RATS; DIHYDRATE KAD-1229;
Keywords:
KAD-1229; POTENT HYPOGLYCEMIC EFFECT; -3-(CIS-HEXAHYDROISOINDOLIN-2-YLCARBONYL)PROPIONIC ACID;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
15
Recensione:
Indirizzi per estratti:
Citazione:
T. Yamaguchi et al., "PREPARATION OF OPTICALLY-ACTIVE SUCCINIC ACID-DERIVATIVES - III - REGIOSELECTIVE CONDENSATION-REACTIONS OF OPTICALLY-ACTIVE 2-SUBSTITUTED SUCCINIC ACIDS WITH DIIMIDAZOLIDE", Yakugaku zasshi, 118(6), 1998, pp. 248-255

Abstract

We investigated the large scale synthesis of monocalcium bis -(cis-hexahydroisoindolin-2-ylcarbonyl)propionate] dihydrate (KAD-1229), whichhas a potent hypoglycemic effect, in a single reaction vessel. -3-(cis-hexahydroisoindolin-2-ylcarbonyl)propionic acid (7) was directly obtainable from (S)-2-benzylsuccinic acid (2) and cis-hexahydroisoindoline (4), without the isolation of intermediates by the method using thionyldiimidazote (9) and/or diimidazolide of the acid 2. Sequential reaction of imidazole with thionyl chloride, 2, and 4, followed by acid catalyzed hydrolysis gave amide-carboxylic acid 7 in 86% overall yield. The acid 7 was treated with 2 N NaOH, followed by the treatment with calcium chloride to give KAD-1229 in 91% yield.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 25/11/20 alle ore 04:34:20