Crystallization-Induced Dynamic Resolution toward the Synthesis of (S)-7-Amino-5H,7H-dibenzo[b,d]-azepin-6-one: An Important Scaffold for γ-Secretase Inhibitors
Тип публикации: Journal Article
Дата публикации: 2016-10-05
SCImago Q1
WOS Q1
БС1
SJR: 0.876
CiteScore: 5.8
Impact factor: 3.3
ISSN: 10836160, 1520586X
Organic Chemistry
Physical and Theoretical Chemistry
Краткое описание
An enantioselective synthesis of (S)-7-amino-5H,7H-dibenzo[b,d]azepin-6-one (S-1) is described. The key step in the sequence involved crystallization-induced dynamic resolution (CIDR) of compound 7 using Boc-d-phenylalanine as a chiral resolving agent and 3,5-dichlorosalicylaldehyde as a racemization catalyst to afford S-1 in 81% overall yield with 98.5% enantiomeric excess.
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Karmakar S. et al. Crystallization-Induced Dynamic Resolution toward the Synthesis of (S)-7-Amino-5H,7H-dibenzo[b,d]-azepin-6-one: An Important Scaffold for γ-Secretase Inhibitors // Organic Process Research and Development. 2016. Vol. 20. No. 10. pp. 1717-1720.
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Karmakar S., Byri V., Gavai A. V., Rampulla R., Mathur A., Gupta A. Crystallization-Induced Dynamic Resolution toward the Synthesis of (S)-7-Amino-5H,7H-dibenzo[b,d]-azepin-6-one: An Important Scaffold for γ-Secretase Inhibitors // Organic Process Research and Development. 2016. Vol. 20. No. 10. pp. 1717-1720.
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TY - JOUR
DO - 10.1021/acs.oprd.6b00207
UR - https://doi.org/10.1021/acs.oprd.6b00207
TI - Crystallization-Induced Dynamic Resolution toward the Synthesis of (S)-7-Amino-5H,7H-dibenzo[b,d]-azepin-6-one: An Important Scaffold for γ-Secretase Inhibitors
T2 - Organic Process Research and Development
AU - Karmakar, Sukhen
AU - Byri, Vijay
AU - Gavai, Ashvinikumar V
AU - Rampulla, Richard
AU - Mathur, Arvind
AU - Gupta, Anuradha
PY - 2016
DA - 2016/10/05
PB - American Chemical Society (ACS)
SP - 1717-1720
IS - 10
VL - 20
SN - 1083-6160
SN - 1520-586X
ER -
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@article{2016_Karmakar,
author = {Sukhen Karmakar and Vijay Byri and Ashvinikumar V Gavai and Richard Rampulla and Arvind Mathur and Anuradha Gupta},
title = {Crystallization-Induced Dynamic Resolution toward the Synthesis of (S)-7-Amino-5H,7H-dibenzo[b,d]-azepin-6-one: An Important Scaffold for γ-Secretase Inhibitors},
journal = {Organic Process Research and Development},
year = {2016},
volume = {20},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://doi.org/10.1021/acs.oprd.6b00207},
number = {10},
pages = {1717--1720},
doi = {10.1021/acs.oprd.6b00207}
}
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Karmakar, Sukhen, et al. “Crystallization-Induced Dynamic Resolution toward the Synthesis of (S)-7-Amino-5H,7H-dibenzo[b,d]-azepin-6-one: An Important Scaffold for γ-Secretase Inhibitors.” Organic Process Research and Development, vol. 20, no. 10, Oct. 2016, pp. 1717-1720. https://doi.org/10.1021/acs.oprd.6b00207.
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