A facile method for the synthesis of 2-(3-hydroxy-1-adamantyl)-2-oxoacetic acid and it's optimization.

Wang, Hui-Fei; Gan, Run; Zhou, Jing; Liao, Qi; Wang, Tian-Bao; Zhong, Cai-Ling; Xiang, Yuan-Yuan; Lin, Hong-Bo; Hu, Xiang-Nan

Wang, Hui-Fei; Gan, Run; Zhou, Jing; Liao, Qi; Wang, Tian-Bao; Zhong, Cai-Ling; Xiang, Yuan-Yuan; Lin, Hong-Bo; Hu, Xiang-Nan.

Afiliação

Wang HF; Department of Pharmacy, Chongqing Medical University, Chongqing, PR China.
Gan R; Bishan Area Maternal and child health care Hospital. Bishan, Chongqing, PR China.
Zhou J; Department of Pharmacy, Chongqing Medical University, Chongqing, PR China.
Liao Q; Department of Pharmacy, Chongqing Medical University, Chongqing, PR China.
Wang TB; Department of Pharmacy, Chongqing Medical University, Chongqing, PR China.
Zhong CL; Department of Pharmacy, Chongqing Medical University, Chongqing, PR China.
Xiang YY; Department of Pharmacy, Chongqing Medical University, Chongqing, PR China.
Lin HB; Department of Pharmacy, Chongqing Medical University, Chongqing, PR China.
Hu XN; Department of Pharmacy, Chongqing Medical University, Chongqing, PR China.

Pak J Pharm Sci ; 31(4): 1393-1397, 2018 Jul.

Article em En | MEDLINE | ID: mdl-30033425

ABSTRACT

ABSTRACT

2-(3-hydroxy-1-adamantyl)-2-oxoacetic acid (IV), a key intermediate of saxagliptin for type 2 diabetes mellitus (T2DM), was prepared from 1-adamantanecarboxylic acid(I) via oxidation by potassium permanganate(KMnO4) to afford 3-hydroxy-1-adamantanecarboxylic acid (II), which was treated with a one-pot method to give 1-acetyl-3-hydroxyadamantane (III) followed by oxidation. Some key steps were optimized and the overall yield was about 51%.

Assuntos

Acetatos/síntese química; Adamantano/análogos & derivados; Adamantano/síntese química; Técnicas de Química Sintética/métodos; Dipeptídeos/química; Hipoglicemiantes/síntese química; Acetatos/química; Acetatos/farmacologia; Adamantano/química; Adamantano/farmacologia; Hipoglicemiantes/química; Hipoglicemiantes/farmacologia; Estrutura Molecular; Permanganato de Potássio/química

Buscar no Google

Imprimir

XML

PubMed Links

Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Adamantano / Dipeptídeos / Técnicas de Química Sintética / Hipoglicemiantes / Acetatos Idioma: En Revista: Pak J Pharm Sci Assunto da revista: FARMACIA / FARMACOLOGIA / QUIMICA Ano de publicação: 2018 Tipo de documento: Article

Buscar no Google

Imprimir

XML

PubMed Links