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Methanol solvate of doripenem intermediate and preparation method thereof

A technology of methanol solvate and doripenem, which is applied in the direction of organic chemistry, can solve the problems of refining, purification, and storage difficulties, and achieve the effect of simple and reliable preparation method, good stability, and easy storage

Active Publication Date: 2009-12-30
SHANGHAI INST OF PHARMA IND +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The technical problem to be solved by the present invention is to overcome the defect that the existing compound of formula I—the doripenem intermediate is an amorphous compound, and its refining, purification, and preservation are difficult, and a kind of doripenem intermediate is provided. Methanol solvate, which is a crystalline compound, is easy to store, easy to operate, good in stability, and high in purity; and its preparation method is simple and reliable, and is suitable for industrial implementation

Method used

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  • Methanol solvate of doripenem intermediate and preparation method thereof
  • Methanol solvate of doripenem intermediate and preparation method thereof
  • Methanol solvate of doripenem intermediate and preparation method thereof

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Embodiment 1～13

[0022] The conditions for preparing methanol solvates with different soluble solvents and methanol are listed in Table 1, and the specific operation is as follows: 0.1 g of amorphous powder of Compound I is dissolved in a soluble solvent, and after the solution is dissolved, methanol is continuously added thereto , stirred, methanol solvate was precipitated. Example 13 is the condition for recrystallizing the methanol solvate obtained in Example 12.

[0023] Table 1

[0024] no

Soluble

agent

Dosage

/ ml

insoluble

solvent

Dosage

/ ml

stirring temperature

/ °C

Stiring time

/ h

purity

(%)

1

ethyl acetate

0.1

Methanol

0.2

15

12

99.1

2

Dichloromethane

0.1

Methanol

0.2

15

12

99.3

3

DMF

0.2

Methanol

0.4

15

12

98.1

4

ethyl acetate

0.2

Methanol

...

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Abstract

The invention discloses a methanol solvate of a doripenem intermediate as shown by a formula I and a preparation method thereof, wherein PNB in an intermediate I represents para-nitrobenzyl, and PNZ represents para-nitro-carbobenzoxygroup. The methanol solvate has the advantages of high purity, good stability, and easy operation and storage; and the preparation method is simple and reliable, and is suitable for industrial implementation.

Description

technical field [0001] The invention relates to a methanol solvate of a doripenem intermediate and a preparation method thereof. Background technique [0002] A pyrrolidinylthiocarbapenem derivative, commonly known as doripenem (compound II), is a known broad-spectrum antibiotic. Compound I is a synthetic intermediate of compound II. In previous reports, this compound is amorphous, and a specific crystalline form has not been isolated. However, there are many difficulties in the refinement, purification, preservation and deprotection of the amorphous compound to obtain high-purity compound II. It is well known that in chemical synthesis processes, especially in industrial manufacturing processes, it is preferable that the compounds produced by a certain method are of high purity or can be isolated and refined into a crystalline form which is easy to handle. [0003] [0004] In compound I, PNB represents p-nitrobenzyl, and PNZ represents p-nitrobenzyloxycarbonyl. [00...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D477/20
Inventor 朱雪焱袁哲东刘相奎曹旭峰
Owner SHANGHAI INST OF PHARMA IND
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