| Autor: |
Dattatray G, Deshmukh, Mukund N, Bangal, Mukunda R, Patekar, Vijay J, Medhane, Vijayavitthal Thippannachar, Mathad |
| Rok vydání: |
2018 |
| Předmět: |
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| Zdroj: |
Acta chimica Slovenica. 65(1) |
| ISSN: |
1318-0207 |
| Popis: |
The present work describes investigation of mechanistic pathway for trimethyl borate mediated amidation of (R)-mandelic acid (3) with 4-nitophenylethylamine (2) to provide (R)-2-hydroxy-N-[2-(4-nitrophenyl)ethyl]-2-phenylacetamide (4) during mirabegron synthesis. Plausible reaction mechanism is proposed by isolating and elucidating the active α-hydroxy ester intermediate 16 from the reaction mass. Trimethyl borate mediated approach proved to be selective in providing 4 without disturbing α-hydroxyl group and stereochemistry of the chiral center, and is also a greener, more economic and production friendly over the reported methods. The developed approach is rapid and efficient for the preparation of 4 with an overall yield of 85-87% and around 99.0% purity by HPLC at scale. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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