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    Method for photocleavage of amide bonds
    1.
    发明授权
    Method for photocleavage of amide bonds 有权

    公开(公告)号：US11845708B2

    公开(公告)日：2023-12-19

    申请号：US17486807

    申请日：2021-09-27

    申请人： NANJING TECH UNIVERSITY

    发明人： Xiaoqiang Chen ,  Tingwen Wei ,  Jing Wang ,  Yanyan Wang

    IPC分类号： C07C227/04 ,  C07D209/20 ,  C07D235/22 ,  C07D403/06

    CPC分类号： C07C227/04 ,  C07D209/20 ,  C07D235/22 ,  C07D403/06

    摘要： The present disclosure provides a method for photocleavage of an amide bond, the method has mild reaction conditions and can realize the cleavage of amide bonds by using light. The method comprises the following steps: subjecting 2,4-dinitrofluorobenzene to a reaction with an amino group of a substance represented by structural formula I with an α-amino acid at the end to produce a compound 1 represented by structural formula II; then under light irradiation, subjecting the compound 1 to a cleavage reaction of amide bond;




    Wherein, R1 is the side chain group of α-amino acid; R2 is: aryl, aliphatic hydrocarbon, —CH(R)—COOH or polypeptide.

    PROCESS FOR THE PREPARATION OF IOPAMIDOL
    3.
    发明申请
    PROCESS FOR THE PREPARATION OF IOPAMIDOL 审中-公开

    公开(公告)号：US20190071392A1

    公开(公告)日：2019-03-07

    申请号：US15912772

    申请日：2018-03-06

    申请人： BRACCO IMAGING S.P.A.

    发明人： Elisa BATTISTINI ,  Federica BUONSANTI ,  Daniela IMPERIO ,  Luciano LATTUADA ,  Roberta NAPOLITANO

    IPC分类号： C07C231/14 ,  C07F5/02 ,  C07C231/12 ,  C07C227/04 ,  C07C201/12 ,  C07C231/02 ,  C07F5/05 ,  C07F5/04 ,  C07C237/46

    CPC分类号： C07C231/14 ,  C07C201/12 ,  C07C227/04 ,  C07C231/02 ,  C07C231/12 ,  C07C237/46 ,  C07F5/025 ,  C07F5/04 ,  C07F5/05 ,  Y02P20/55 ,  Y02P20/582

    摘要： The present invention discloses a process for the preparation of Iopamidol of formula (II) and comprising the following steps: a) reacting the Compound (I) wherein X is OR2 or R3, and wherein R2 and R3 are a Ci-C6 linear or branched alkyl, C3-C6 cycloalkyl, C6 aryl, optionally substituted with a group selected from the group consisting of methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, t-butyl and phenyl, with the acylating agent (S)-2-(acetyloxy)propanoyl chloride in a reaction medium to provide the acetyloxy derivative of Compound (I); b) hydrolyzing the intermediate from step a) with an aqueous solution at a pH comprised from 0 to 7, by adding water or a diluted alkaline solution such as sodium hydroxide or potassium hydroxide, freeing the hydroxyls from the boron-containing protective groups, obtaining the N—(S)-2-(acetyloxy)propanoyl derivative of Compound (II); c) alkaline N hydrolysis to restore the (S)-2-(hydroxy)propanoyl group and to obtain Iopamidol (II) and optional recovery of the boron derivative from the solution obtained in step b). The boron-containing protective group is versatile, efficient and recyclable. A one-pot synthesis, without intermediate isolation is provided, leading to a decreasing of recovered and recycled solvents and a significant increasing in the yield, representing a significant advantage in terms of cost-effectiveness of the entire process and environmental awareness.