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Preparation method for Arbekacin intermediate Dibekacin

A technology of rebekacin and arbekacin, which is applied in the field of preparation of arbekacin intermediate dibekacin, can solve the problems of complicated process and long synthesis route of dibekacin, and achieves simplified synthesis process, The effect of high yield and high purity

Active Publication Date: 2017-07-14
CHANGZHOU FANGYUAN PHARMA +1
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Problems solved by technology

[0009] The synthesis route of dibekacin disclosed in the above-mentioned documents is long and the process is complex

Method used

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  • Preparation method for Arbekacin intermediate Dibekacin
  • Preparation method for Arbekacin intermediate Dibekacin
  • Preparation method for Arbekacin intermediate Dibekacin

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Embodiment 1

[0025] The preparation method of the arbekacin intermediate dibekacin of the present embodiment comprises the following steps:

[0026] ① For the ring-forming protection of the hydroxyl group at the 4″ and 5″ positions of kanamycin B, the reaction formula involved is as follows.

[0027]

[0028] Firstly, 21.64g (114mmol, 5.5eq) of p-toluenesulfonic acid monohydrate was dehydrated under vacuum at 90°C, and after dehydration was completed, it was cooled to room temperature for use.

[0029] Dissolve the dehydrated p-toluenesulfonic acid in 100 mL of dimethylformamide (hereinafter referred to as DMF), and continue to add 10 g (20 mmol) of dry kanamycin B (code name KB) and 12.4 mL ( 82mmol, 4eq, eq=equivalent (molar equivalent) PhCH(OMe) 2 . The obtained reaction material was stirred at room temperature in a rotary evaporator equipped with double-pump vacuuming for 2.5h-4h (3h in this example), and the second vacuum pump could be turned off in case of severe evaporation. F...

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Abstract

The invention discloses a preparation method for an Arbekacin intermediate Dibekacin. P-toluenesulfonic acid, kanamycin B and PhCH(OMe)2 are first mixed to react, forming ring protection on the hydroxyl groups at sites 4'' and 5'' of kanamycin B, R groups (R=BnSO2) are then used for replacing hydrogen atoms of -NH2 groups at sites 1, 3, 2', 5' and 3'' and -OH groups at sites 3', 4' and 2'', -OR groups at sites 3' and 4' are then removed and ring opening is carried out at sites 4'' and 5'', and finally, R(R=BnSO2) group protection is removed, so that Dibekacin is obtained. The route of the preparation method for Dibekacin disclosed by the invention is simple, and the synthesis process is simplified; moreover, final yield is high, the yield reaches 53.4 percent, the purity of obtained Dibekacin is high, and the purity is 98 percent. The protective reagent dimethoxymethylbenzene used in the first step is cheap and easy to obtain.

Description

technical field [0001] The invention relates to an organic synthesis method, in particular to a preparation method of dibekacin, an arbekacin intermediate. Background technique [0002] Arbekacin (Arbekacin) is a double chemically modified semi-synthetic aminoglycoside antibiotic, which is mainly used to treat infections caused by various drug-resistant bacteria, especially for the treatment of methicillin-resistant Staphylococcus aureus (MRSA). ) infection, in February 2005, arbekacin was listed by the World Health Organization as one of the most important antibiotics in the 21st century. 3', 4'-dideoxykanamycin B (Debekacin) is an important intermediate of arbekacin, and debekacin itself is also a semi-synthetic antibiotic product already on the market. [0003] The chemical structural formulas of Arbekacin and Debekacin are as follows: [0004] [0005] Regarding the preparation method of debekacin (Debekacin), Chinese patent document CN102786564A (application number...

Claims

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Application Information

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IPC IPC(8): C07H15/234C07H1/00C07H1/06
CPCC07H1/00C07H1/06C07H15/234
Inventor 谢尔盖杜德金
Owner CHANGZHOU FANGYUAN PHARMA
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