多克制备 BRD4780 对映异构体和绝对立体化学构型的确定。
Multigram Preparation of BRD4780 Enantiomers and Assignment of Absolute Stereochemistry.
机构信息
Center for the Development of Therapeutics, Broad Institute of MIT and Harvard, Cambridge, Massachusetts 02142, United States.
BioTools, Inc., 17546 Bee Line Highway, Jupiter Florida 33458, United States.
出版信息
J Org Chem. 2021 Mar 5;86(5):4281-4289. doi: 10.1021/acs.joc.0c02520. Epub 2021 Feb 22.
The development of a multigram synthesis of 3--isopropylbicyclo[2.2.1]heptan-2--amine hydrochloride () (also known as BRD4780 and AGN-192403) is described. The process involves protection of the amine as 4-nitrobenzyl carbamate, pNZ, which enables chiral SFC chromatography. The absolute configuration (AC) of the individual enantiomers has been determined by Mosher's amide method, VCD spectroscopy, and X-ray crystallography. We highlight the VCD approach as a rapid and effective means of AC determination that can be deployed directly on the target compounds.
本文描述了 3--异丙基双环[2.2.1]庚烷-2--胺盐酸盐（）（也称为 BRD4780 和 AGN-192403）的多克合成开发。该过程涉及将胺保护为 4-硝基苄基氨基甲酸酯（pNZ），这使得手性 SFC 色谱法成为可能。通过 Mosher 的酰胺法、VCD 光谱法和 X 射线晶体学确定了各个对映体的绝对构型（AC）。我们强调了 VCD 方法作为一种快速有效的 AC 确定方法，可直接用于目标化合物。
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