Practical and scalable synthesis of beclomethasone dipropionate
[Display omitted] •Practical and scalable approach to synthesize beclomethasone dipropionate.•Readily available and cost-effective intermediate DB-11 as the starting material.•Optimized consistent conversion of DB-11 to beclomethasone with high purity.•A one-pot conversion of beclomethasone to beclo...
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Published in | Steroids Vol. 177; pp. 108948 - 108953 |
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Main Authors | , , , , , , , , , , , , , |
Format | Journal Article |
Language | English |
Published |
NEW YORK
Elsevier Inc
01.01.2022
Elsevier |
Subjects | |
Online Access | Get full text |
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Summary: | [Display omitted]
•Practical and scalable approach to synthesize beclomethasone dipropionate.•Readily available and cost-effective intermediate DB-11 as the starting material.•Optimized consistent conversion of DB-11 to beclomethasone with high purity.•A one-pot conversion of beclomethasone to beclomethasone dipropionate.
Beclomethasone dipropionate (1) is a synthetic corticosteroid with anti-inflammatory, antipruritic, and anti-allergy properties. It is widely used to treat asthma, allergic rhinitis, and dermatoses. However, existing synthetic routes to this active pharmaceutical ingredient (API) contain steps resulting in low and/or inconsistent yields, and use obsolete reagents. Such inconsistencies coupled with a lack of reliable experimental data makes laboratory-scale and large-scale synthesis of this API difficult and time-consuming. In this paper, we report a practical and scalable approach to synthesize 1 from the readily available steroidal intermediate, 16β-methyl epoxide (3, DB-11). A gram-scale to kilogram-scale synthesis of 1 was achieved with 82% yield, using a cost-effective and scalable methodology. Selective propionylation of the hydroxyl groups at C17 and C21 demonstrate the fact that this approach can be conveniently implemented in fine chemical industries. |
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ISSN: | 0039-128X 1878-5867 |
DOI: | 10.1016/j.steroids.2021.108948 |