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Method for synthesizing adefovir dipivoxil ester

A technology of adefovir dipivoxil and a synthetic method, which is applied in the field of drug synthesis, can solve the problems of complex process, long reaction steps, low yield and the like, and achieves high yield, short synthetic route steps and high total yield. Effect

Active Publication Date: 2009-10-28
FUJIAN COSUNTER PHARMA CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0032] Above method reaction step is long, and technique is complicated, and yield is low

Method used

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  • Method for synthesizing adefovir dipivoxil ester
  • Method for synthesizing adefovir dipivoxil ester
  • Method for synthesizing adefovir dipivoxil ester

Examples

Experimental program
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Embodiment 1

[0056] 1. Synthesis of 1-chloro-2-chloromethoxyethane (3)

[0057] Feeding amount:

[0058]

[0059] Steps:

[0060] Suspend 30.0 g of paraformaldehyde (2) in 80.5 g of 2-chloroethanol (1), stir at room temperature, pass through anhydrous hydrogen chloride gas for 22 hours, the solid dissolves, separate the water layer, add anhydrous calcium chloride 20.0 g to the organic layer g dried, blown with nitrogen for 4h, filtered, and distilled under reduced pressure to collect 90.6g of bp62-66°C / 29Mg slightly yellow transparent liquid (3), yield 70.2%. Quality control method: bp62-66℃ / 29mmHa.

[0061] Attachment: Preparation of anhydrous hydrogen chloride gas: Mix concentrated hydrochloric acid and sodium chloride evenly, slowly add concentrated sulfuric acid dropwise, and the generated hydrogen chloride gas is dried by concentrated sulfuric acid.

[0062] 2. 2-Chloroethoxymethylphosphonic acid dimorpholine ester (4)

[0063] Feeding ratio

[0064]

[0065] (3) Stir and h...

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Abstract

The present invention relates to a method for synthesizing medicine, in particular to a method for synthesizing adefovir dipivoxil. The operation steps of the method are as follows: Step 1, chloromethylation reaction of 2-chloroethanol with paraformaldehyde and anhydrous hydrogen chloride Obtain 1-chloro-2-chloromethoxyethane; Step 2, 1-chloro-2-chloromethoxyethane reacts with trimorpholine phosphite to obtain 2-chloroethoxymethylphosphonic acid dimorpholine Ester; Step 3, 2-chloroethoxymethyl phosphonic acid dimorpholine ester; in DMF through anhydrous K2CO3 catalyzed condensation with adenine to obtain 9-(2-dimorpholinylphosphonomethoxyethyl) adenine ; Step 4, 9-(2-dimorpholinylphosphonomethoxyethyl) adenine is hydrolyzed with hydrochloric acid in DMF and water to obtain 9-(2-phosphonomethoxyethyl) adenine; Step 5, 9- (2-phosphonomethoxyethyl) adenine reacts with chloromethyl pivalate in DMF catalyzed by triethylamine to obtain adefovir dipivoxil.

Description

Technical field: [0001] The invention relates to a drug synthesis method, in particular to a synthesis method of anti-hepatitis B drug adefovir dipivoxil. Background technique: [0002] Adefovir dipivoxil is a new type of oral broad-spectrum antiviral drug, which inhibits viral transcription and replication by inhibiting viral DNA polymerase and cryotron transcriptase, and has a strong inhibitory effect on hepatitis B virus and HIV. It also has a strong inhibitory effect on lamivudine and famciclovir-resistant hepatitis B virus. It is a ring-opening nucleoside reverse transcriptase inhibitor and a prodrug of adefovir (PMEA). The degree of adefovir dipivoxil is larger than that of adefovir dipivoxil. Adefovir dipivoxil was developed by Gilead Sciences of the United States. It was approved by the U.S. FDA on September 20, 2002 for the first time. Its English name is Adefovir Dipivoxil, its trade name is Hepsera, and its chemical name is 9-{2 -[bis(pivaloyloxymethoxy)phosphono...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/6561
Inventor 陈国华康惠燕
Owner FUJIAN COSUNTER PHARMA CO LTD
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