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Title: Quantum chemistry-assisted synthesis route development

Abstract

We have been investigating “quantum chemistry-assisted synthesis route development” using in silico screenings and applied the method to several targets. Another example was conducted to develop synthesis routes for a urea derivative, namely 1-(4-(trifluoromethyl)-2-oxo-2H-chromen-7-yl)urea. While five synthesis routes were examined, only three routes passed the second in silico screening. Among them, the reaction of 7-amino-4-(trifluoromethyl)-2H-chromen-2-one and O-methyl carbamate with BF{sub 3} as an additive was ranked as the first choice for synthetic work. We were able to experimentally obtain the target compound even though its yield was as low as 21 %. The theoretical result was thus consistent with that observed. The summary of transition state data base (TSDB) is also provided. TSDB is the key to reducing time of in silico screenings.

Authors:
;  [1];  [2]
  1. Graduate School of Science and Engineering, Yamaguchi University, Tokiwadai, Ube, Yamaguchi 755-8611 (Japan)
  2. Graduate School of Medicine, Yamaguchi University, Yamaguchi, Yamaguchi 753-8512 (Japan)
Publication Date:
OSTI Identifier:
22499137
Resource Type:
Journal Article
Journal Name:
AIP Conference Proceedings
Additional Journal Information:
Journal Volume: 1702; Journal Issue: 1; Conference: ICCMSE 2015: International conference of computational methods in sciences and engineering 2015, Athens (Greece), 20-23 Mar 2015; Other Information: (c) 2015 AIP Publishing LLC; Country of input: International Atomic Energy Agency (IAEA); Journal ID: ISSN 0094-243X
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; ADDITIVES; BORON FLUORIDES; CARBAMATES; CHEMISTRY; SCREENING; SYNTHESIS; UREA

Citation Formats

Hori, Kenji, Sumimoto, Michinori, and Murafuji, Toshihiro. Quantum chemistry-assisted synthesis route development. United States: N. p., 2015. Web. doi:10.1063/1.4938827.
Hori, Kenji, Sumimoto, Michinori, & Murafuji, Toshihiro. Quantum chemistry-assisted synthesis route development. United States. https://doi.org/10.1063/1.4938827
Hori, Kenji, Sumimoto, Michinori, and Murafuji, Toshihiro. 2015. "Quantum chemistry-assisted synthesis route development". United States. https://doi.org/10.1063/1.4938827.
@article{osti_22499137,
title = {Quantum chemistry-assisted synthesis route development},
author = {Hori, Kenji and Sumimoto, Michinori and Murafuji, Toshihiro},
abstractNote = {We have been investigating “quantum chemistry-assisted synthesis route development” using in silico screenings and applied the method to several targets. Another example was conducted to develop synthesis routes for a urea derivative, namely 1-(4-(trifluoromethyl)-2-oxo-2H-chromen-7-yl)urea. While five synthesis routes were examined, only three routes passed the second in silico screening. Among them, the reaction of 7-amino-4-(trifluoromethyl)-2H-chromen-2-one and O-methyl carbamate with BF{sub 3} as an additive was ranked as the first choice for synthetic work. We were able to experimentally obtain the target compound even though its yield was as low as 21 %. The theoretical result was thus consistent with that observed. The summary of transition state data base (TSDB) is also provided. TSDB is the key to reducing time of in silico screenings.},
doi = {10.1063/1.4938827},
url = {https://www.osti.gov/biblio/22499137}, journal = {AIP Conference Proceedings},
issn = {0094-243X},
number = 1,
volume = 1702,
place = {United States},
year = {Thu Dec 31 00:00:00 EST 2015},
month = {Thu Dec 31 00:00:00 EST 2015}
}