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    METHOD FOR THE CONTINUOUS FLOW SYNTHESIS OF (R)-4-HALO-3-HYDROXY-BUTYRATE
    1.
    发明申请
    METHOD FOR THE CONTINUOUS FLOW SYNTHESIS OF (R)-4-HALO-3-HYDROXY-BUTYRATE 有权

    公开(公告)号：US20220056489A1

    公开(公告)日：2022-02-24

    申请号：US17516894

    申请日：2021-11-02

    Applicant: Fudan University

    Inventor： Fener CHEN ,  Dang CHENG ,  Zedu HUANG ,  Minjie LIU ,  Huashan HUANG ,  Meifen JIANG ,  Lulu WANG

    IPC: C12P7/62 ,  C12M1/02 ,  C12M1/34 ,  C12M1/36 ,  C12M1/00

    Abstract: A method for the continuous flow synthesis of (R)-4-halo-3-hydroxy-butyrate using a micro-reaction system. The micro-reaction system includes a micro-mixer, a certain number of micro-reaction units that are successively connected in series, a pH regulating system and a back pressure valve. The micro-reaction unit is composed of a micro-channel reactor and a pH regulator that are sequentially connected with each other. A substrate solution containing halogenated acetoacetate and a biocatalyst solution are simultaneously pumped into the micro-reaction system to enable continuous flow biocatalytic asymmetric reduction reaction of the halogenated acetoacetate to obtain the target product (R)-4-halo-3-hydroxy-butyrate.

    METHOD FOR PREPARING A KEY INTERMEDIATE FOR THE SYNTHESIS OF STATINS
    2.
    发明申请
    METHOD FOR PREPARING A KEY INTERMEDIATE FOR THE SYNTHESIS OF STATINS 有权

    公开(公告)号：US20220017508A1

    公开(公告)日：2022-01-20

    申请号：US17488276

    申请日：2021-09-28

    Applicant: Fudan University

    Inventor： Fener CHEN ,  Dang CHENG ,  Minjie LIU ,  Zedu HUANG ,  Yuan TAO ,  Jiaqi WANG

    IPC: C07D417/12

    Abstract: Disclosed herein relates to organic synthesis, and more particularly to a method for preparing a key intermediate for the synthesis of statins. The key intermediate is 2-[(4R, 6S)-6-[(benzo[d]thiazol-2-ylthio)methyl]-2,2-di substituted-1,3-dioxan-4-yl] acetate of formula (I): where R1 is a C1-C8 alkyl group, a C3-C8 cycloalkyl group, a monosubstituted or polysubstituted aryl group, or monosubstituted or polysubstituted aralkyl group; R2 is hydrogen, or monosubstituted or polysubstituted C1-C3 alkyl group, or halogen; and R3 and R4 are each independently a C1-C5 alkyl group, a C3-C7 cycloalkyl group, a C3-C7 cycloalkenyl group, a C1-C3 alkoxy group, a C6-C10 aryl group, or C7-C12 aralkyl group. In the method, a halomethyl compound and a thiol reagent are subjected to nucleophilic substitution in an organic solvent to synthesize a thioether, which then undergoes ketal exchange reaction with a carbonyl compound (V) in the presence of an organic acid to obtain a target product.

    FULL CONTINUOUS FLOW PREPARATION METHOD OF 2-METHYL-4-AMINO-5-AMINOMETHYLPYRIMIDINE
    3.
    发明申请
    FULL CONTINUOUS FLOW PREPARATION METHOD OF 2-METHYL-4-AMINO-5-AMINOMETHYLPYRIMIDINE 有权

    公开(公告)号：US20210394150A1

    公开(公告)日：2021-12-23

    申请号：US17467091

    申请日：2021-09-03

    Applicant: Fudan University

    Inventor： Fener CHEN ,  Meifen JIANG ,  Minjie LIU ,  Huashan HUANG ,  Dang CHENG

    IPC: B01J19/00 ,  C07D239/42 ,  B01J25/02

    Abstract: A full continuous flow preparation method of 2-methyl-4-amino-5-aminomethylpyrimidine. A mixed solution of cyanoacetamide, N,N-dimethylformamide and a catalyst is mixed with phosphorus oxychloride in a first micro-mixer, and then the reaction mixture undergoes continuous flow reaction in a microchannel reactor to obtain (dimethylaminomethylene) malononitrile. The reaction mixture is subjected to continuous quenching, extraction and separation, and the organic phase is concentrated, mixed with a methanol solution, and then reacted with an organic base to obtain 2-methyl-4-amino-5-cyanopyrimidine. After the mixed liquid is continuously filtered, the filter cake is dissolved in methanol, mixed with hydrogen in a second micro-mixer, and then transported to a fixed-bed reactor for hydrogenation reaction. The products are concentrated, dried and purified to obtain the desired 2-methyl-4-amino-5-aminomethylpyrimidine.

    FULL CONTINUOUS SYNTHESIS DEVICE AND METHOD FOR METRONIDAZOLE
    4.
    发明公开
    FULL CONTINUOUS SYNTHESIS DEVICE AND METHOD FOR METRONIDAZOLE 审中-公开

    公开(公告)号：US20240270696A1

    公开(公告)日：2024-08-15

    申请号：US18625925

    申请日：2024-04-03

    Applicant: Fudan University

    Inventor： Fener CHEN ,  Minjie LIU ,  Li WAN ,  Yajiao ZHANG ,  Dang CHENG

    IPC: C07D233/94 ,  B01J19/00

    CPC classification number: C07D233/94 ,  B01J19/006 ,  B01J19/0066 ,  B01J19/0093 ,  B01J2219/00033 ,  B01J2219/00768 ,  B01J2219/00783 ,  B01J2219/00864 ,  B01J2219/00867 ,  B01J2219/00889

    Abstract: A full continuous synthesis method of metronidazole is provided. An aqueous glyoxal solution, an aqueous acetaldehyde solution and aqueous ammonia are mixed and reacted to produce a 2-methylimidazole-containing reaction mixture, which is mixed with a nitric acid solution and then reacted in the presence of concentrated sulfuric acid to obtain a 2-methyl-5-nitroimidazole-containing reaction mixture. The 2-methyl-5-nitroimidazole-containing reaction mixture is divided by a splitter, such that one part is used to replace concentrated sulfuric acid, and the other part is mixed with formic acid, and undergoes a ring-opening reaction with ethylene oxide to obtain a metronidazole solution. The metronidazole solution is adjusted to pH 2-6 and filtered to obtain a filtrate, which is adjusted to pH 8-14 and filtered to obtain a crude product. The crude product is subjected to decoloring, crystallization, filtration and drying to obtain pure metronidazole with a purity greater than 99.9%.

    FULL CONTINUOUS-FLOW PREPARATION METHOD OF L-CARNITINE
    8.
    发明申请
    FULL CONTINUOUS-FLOW PREPARATION METHOD OF L-CARNITINE 有权

    公开(公告)号：US20220267253A1

    公开(公告)日：2022-08-25

    申请号：US17741112

    申请日：2022-05-10

    Applicant: Fudan University

    Inventor： Fener CHEN ,  Minjie LIU ,  Meifen JIANG ,  Dang CHENG ,  Chao YU ,  Huashan HUANG

    IPC: C07C227/12 ,  B01J19/00

    Abstract: A full continuous-flow preparation method of L-carnitine, including: mixing chlorine gas and a diketene solution via a first micromixer followed by transportation to a first microchannel reactor for continuous chlorination and esterification reaction to obtain 4-chloroacetoacetate; feeding the 4-chloroacetoacetate and a reductase to a second micromixer and a second microchannel reactor in sequence for continuous catalytic reaction to obtain (R)-4-chloro-3-hydroxybutyrate; simultaneously transporting the (R)-4-chloro-3-hydroxybutyrate and a trimethylamine solution to a third micromixer and a third microchannel reactor for continuous substitution and hydrolysis reaction; and subjecting the reaction mixture to desalination and concentration to obtain the L-carnitine.

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