volume 14 issue 3 pages 553-561

Kilogram Synthesis of a LFA-1/ICAM Inhibitor

Albert J Delmonte
Robert E Waltermire
Fan Yu
Douglas D Mcleod
Zhinong Gao
Kirsten D Gesenberg
Kevin P Girard
Miguel Rosingana
Xuebao Wang
Jennifer Kuehne Willmore
Alan D Braem
John A. Castoro
Publication typeJournal Article
Publication date2010-05-21
scimago Q1
wos Q1
SJR0.865
CiteScore5.4
Impact factor3.5
ISSN10836160, 1520586X
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
The process development and the kilogram-scale synthesis of BMS-587101 (1) are described. The synthesis features a [3 + 2] azomethine ylide cycloaddition to efficiently build the spirocyclic core in a diastereoselective fashion followed by a classical resolution which affords the desired enantiomer in >98% enantiomeric excess. The target was prepared in four steps in an overall yield of 22%.
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GOST Copy
Delmonte A. J. et al. Kilogram Synthesis of a LFA-1/ICAM Inhibitor // Organic Process Research and Development. 2010. Vol. 14. No. 3. pp. 553-561.
GOST all authors (up to 50) Copy
Delmonte A. J., Waltermire R. E., Yu F., Mcleod D. D., Gao Z., Gesenberg K. D., Girard K. P., Rosingana M., Wang X., Kuehne Willmore J., Braem A. D., Castoro J. A. Kilogram Synthesis of a LFA-1/ICAM Inhibitor // Organic Process Research and Development. 2010. Vol. 14. No. 3. pp. 553-561.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1021/op9003168
UR - https://doi.org/10.1021/op9003168
TI - Kilogram Synthesis of a LFA-1/ICAM Inhibitor
T2 - Organic Process Research and Development
AU - Delmonte, Albert J
AU - Waltermire, Robert E
AU - Yu, Fan
AU - Mcleod, Douglas D
AU - Gao, Zhinong
AU - Gesenberg, Kirsten D
AU - Girard, Kevin P
AU - Rosingana, Miguel
AU - Wang, Xuebao
AU - Kuehne Willmore, Jennifer
AU - Braem, Alan D
AU - Castoro, John A.
PY - 2010
DA - 2010/05/21
PB - American Chemical Society (ACS)
SP - 553-561
IS - 3
VL - 14
SN - 1083-6160
SN - 1520-586X
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2010_Delmonte,
author = {Albert J Delmonte and Robert E Waltermire and Fan Yu and Douglas D Mcleod and Zhinong Gao and Kirsten D Gesenberg and Kevin P Girard and Miguel Rosingana and Xuebao Wang and Jennifer Kuehne Willmore and Alan D Braem and John A. Castoro},
title = {Kilogram Synthesis of a LFA-1/ICAM Inhibitor},
journal = {Organic Process Research and Development},
year = {2010},
volume = {14},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://doi.org/10.1021/op9003168},
number = {3},
pages = {553--561},
doi = {10.1021/op9003168}
}
MLA
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MLA Copy
Delmonte, Albert J., et al. “Kilogram Synthesis of a LFA-1/ICAM Inhibitor.” Organic Process Research and Development, vol. 14, no. 3, May. 2010, pp. 553-561. https://doi.org/10.1021/op9003168.