Preparing method for D(-)-sulbenicillin disodium

A technology for sulfobenicillin sodium and sulfobenicillin is applied in the field of drug synthesis, which can solve the problems of complicated purification process, long reaction steps, unsuitable industrial production and the like, and achieves improved product purity, mild reaction conditions, and no sulfur dioxide pollution. Effect

Inactive Publication Date: 2016-01-06
ZHEJIANG ESIGMA BIOTECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction steps are long, the purification process is cumbersome, and it is not suitable for industrial production

Method used

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  • Preparing method for D(-)-sulbenicillin disodium
  • Preparing method for D(-)-sulbenicillin disodium
  • Preparing method for D(-)-sulbenicillin disodium

Examples

Experimental program
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Effect test

Embodiment 1

[0026] (1) Preparation of dichloroethane solution of D(-)-sulfophenylacetyl chloride

[0027] Add 26.2g (0.121mol) D(-)-sulfophenylacetic acid, 78.6g solvent dichloroethane and 0.439g (0.006mol) catalyst dimethylformamide in the reaction vessel, slowly add 18.6ml2mol at 0°C / LBTC / C 2 h 4 Cl 2 Solution, after addition, reacted at room temperature for 1.5 hours, recovered the solvent by distillation under reduced pressure and removed hydrogen chloride gas to obtain 26.57g of D(-)-sulfophenylacetyl chloride, the HPLC purity was 97.75%, and the yield was 91.5%, and then 26.57g was added Dichloroethane, prepared as a dichloroethane solution of D(-)-sulfophenylacetyl chloride with a mass fraction of 50%.

[0028] (2) Preparation of D(-)-Sulbenicillin Sodium

[0029] Add 41g acetone, 20.5g75% ethanol and 20.5g (0.095mol) 6-aminopenicillanic acid in the reaction vessel, add trimethylamine until the pH of the reaction system is 7 at 10°C, stir until the 6-aminopenicillanic acid is ...

Embodiment 2-3D

[0030] The dichloroethane solution preparation of embodiment 2-3D (-)-sulfophenylacetyl chloride

[0031] Adopt the same operating method as Example 1 (1) to prepare the dichloroethane solution of D(-)-sulfophenylacetyl chloride, the difference is BTC / C 2 h 4 Cl 2 Amount of solution and solvent dichloroethane, BTC / C 2 h 4 Cl 2 The dripping temperature of solution, reaction time, gained experimental result is shown in Table 1:

[0032] Table 1:

[0033]

Embodiment 4-5D

[0034] The preparation of embodiment 4-5D (-)-sulfbenicillin sodium

[0035] Adopt the same operating method as Example 1 (1) to prepare D (-)-sulfabenicillin sodium, the difference is the amount of 6-aminopenicillanic acid, trimethylamine adding temperature and reaction time, the experimental results obtained are shown in Table 2:

[0036] Table 2:

[0037]

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Abstract

The invention provides a preparing method for D(-)-sulbenicillin disodium. The preparing method includes the concrete operation steps that D(-)-sulfophenylacetic acid, dichloroethane and a catalyst dimethylformamide are added into a reaction container, a BTC / C2H4Cl2 solution serves as an acylating chlorination agent, and a dichloroethane solution of D(-)-sulfophenylacetyl chloride is obtained through preparation; D(-)-sulfophenylacetyl chloride and 6-aminopenicillanic acid are prepared into D(-)-sulbenicillin disodium through condensation and refining. The BTC / C2H4Cl2 solution is adopted as the acylating chlorination agent, reaction efficiency is high, the number of side reactions is small, sulfur dioxide pollution is avoided, and the preparing method is of significance in environment-friendly production; acetone and 75% ethyl alcohol are adopted as solvent in the condensation reaction, the pH value is controlled to be seven through trimethylamine, the condensation reaction is carried out at about 10 DEG C, reaction conditions are moderate, the process is simple and easy to operate, the purity and the yield of the obtained D(-)-sulbenicillin disodium are high, and the preparing method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, and in particular relates to a preparation method of D(-)-sulfbenicillin sodium. Background technique [0002] D(-)-Sulbenicillin sodium, the English name is sulbenicillindisodium, the Chinese chemical name is: (2S,5R,6R)-3,3-dimethyl-6-(2-phenyl-2-sulfoacetamido )-7-oxo-4-thia-1-azabicyclo[3,2,0]heptane-2-carboxylic acid disodium salt, the molecular formula is C 16 h 16 N 2 Na 2 o 7 S 2 , its structural formula is as follows: [0003] [0004] Sulbenicillin Sodium is a classic semi-synthetic penicillin, white or light yellow powder, odorless, slightly salty, easily soluble in water, easily soluble in methanol, slightly soluble in ethanol. The antibacterial spectrum of sulbenicillin sodium is similar to that of sulbenicillin, and its reaction to enzymes is more stable than that of ampicillin and carbenicillin. Since α-sulfophenylacetic acid has a chiral center, sulfbenicilli...

Claims

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Application Information

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IPC IPC(8): C07D499/62C07D499/16
CPCC07D499/62C07D499/16
Inventor 吴中华张小朋陈贵才徐天华何奇雷闻鸣
Owner ZHEJIANG ESIGMA BIOTECH CO LTD
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