Journal article
Optimized synthesis of indole carboxylate metallo-beta-lactamase inhibitor EBL-3183
- Abstract:
- A new synthetic route for the preparation of the metallo-β-lactamase inhibitor pre-candidate EBL-3183 was developed and carried out on a kilogram scale. The described process starts from a commercially available indole-2-carboxylate and employs an Ellman auxiliary approach coupled with ruthenium-catalyzed stereoselective reduction for the introduction of chirality. The key spirocyclic cyclobutane motif was assembled utilizing an epoxide building block, which was conveniently obtained in diastereomerically pure form. The amount and quality of the prepared final target EBL-3183 were sufficient for the preclinical studies.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
Actions
Access Document
- Files:
-
-
(Preview, Accepted manuscript, pdf, 1.4MB, Terms of use)
-
- Publisher copy:
- 10.1021/acs.oprd.3c00002
Authors
- Publisher:
- American Chemical Society
- Journal:
- Organic Process Research & Development More from this journal
- Volume:
- 27
- Issue:
- 4
- Pages:
- 692–706
- Publication date:
- 2023-03-30
- DOI:
- EISSN:
-
1520-586X
- ISSN:
-
1083-6160
- Language:
-
English
- Keywords:
- Pubs id:
-
1335875
- Local pid:
-
pubs:1335875
- Deposit date:
-
2023-05-19
- ARK identifier:
Terms of use
- Copyright holder:
- American Chemical Society
- Copyright date:
- 2023
- Rights statement:
- © 2023 American Chemical Society
- Notes:
- This is the accepted manuscript version of the article. The final version is available online from American Chemical Society at: https://dx.doi.org/10.1021/acs.oprd.3c00002
If you are the owner of this record, you can report an update to it here: Report update to this record