ChemicalBook CAS DataBase List Oxaliplatin

Oxaliplatin synthesis

4synthesis methods

Product Name:Oxaliplatin
CAS Number:61825-94-3
Molecular formula:C8H12N2O4Pt
Molecular Weight:395.28

An aqueous solution of 5 g of (1R,2R)-(-)-1,2-DiaMinocyclohexane and 18 g of K2(PtCl4) was reacted for 12 h at room temperature to give 12 g of compound (I). 6: 8 g of silver nitrate was added to an aqueous solution of 3 g of compound (I) and stirred for 2-3 h away from light, then 4.8 g of dipotassium oxalate was added and the reaction was carried out for 8 h at room temperature to give oxaliplatin.

144-62-7 Synthesis

144-62-7
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61825-94-3
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$19.00/50mg

Yield:61825-94-3 62.9%

Reaction Conditions:

Stage #1:(1R,2R)-1,2-diaminocyclohexanedichloroplatinum(II) with water;silver nitrate at 20 - 45; for 2.08333 h;
Stage #2:oxalic acid with potassium hydroxide in water; pH=2.9 at 20; for 4 h;Product distribution / selectivity;

Steps:

1; 2; 3
A mixture of 3,88 g of fine powdered DACHPtCI₂ 98% (10 mmol), 1.55 g purified Celite, 3.41 g AgNO₃ 99.5% (20 mmol) and 27 ml pu- rified water was intensively stirred 5 minutes at room temperature and then 2 hours at 45⁰C. The suspension was cooled to 3⁰C and then filtered through the plate with active charcoal. The crude acidic filtrate had the content of silver ions 0.0018 mass.% ,i.e. 18 p.p.m. 0.19 g of Smopex-101 was added to the crude filtrate and the sus- pension was stirred 1 hour at room temperature. The solid fraction was then removed by filtration. The purifying procedure with Smopex-101 was repeated once again and the purified solution was then filtered through an ultrafilter with the porosity 0.22 μm. 1.27 g oxalic acid dihydrate 99.5% (10 mmol) was added to the purified solution, pH value was adjusted to 2.9 by means of 40% solution of KOH₁ the mixture was stirred 4 hours at room temperature and the resulting suspension was cooled to 3⁰C. The final solid oxaliplatin was separated by filtration, washed four times with 5 ml ice water and four times with 5 ml ethanol. Oxaliplatin was dried under nitrogen flow at 40⁰C to the constant weight. The yield of oxaliplatin was 2.80 g (70.5% based on starting DACHPtCI₂). The appearance of the product was white. The content of silver was less than 0.00005 mass %, i.e. 0.5 p.p.m., the content of oxalic acid was 0.04%, the content of platinum(ll) diaqua-complex was 0.08%, and the total content of related impurities was 0.22% (by HPLC method).; Example 2; The same procedure according to Example 1 with exception that 0.39 g Dowex 50x8 in H-cycle was used instead of 0.19 g Smopex- 101 for purifying of the crude filtrate and that time of purification was 2 hours instead of 1 hour.The yield of oxaliplatin was 2,50 g (62.9% based on startingDACHPtCI₂). The appearance of the product was white. The content of silver was 0.0001 mass %, i.e. 1 p.p.m., the content of oxalic acid was 0,04%, the content of platinum(ll) diaqua-complex was 0.09%, and the total content of related impurities was 0.25% (by HPLC method).; Example 3 (comparative, without Celite); The same procedure according to Example 1 with exception that no Celite was used in the procedure. The crude acidic filtrate had the content of silver ions 0.2500 mass.%, i.e. 2500 p.p.m.The yield of oxaliplatin was 2.60 g (65.5% based on starting DACHPtCI₂). The appearance of the product was white. The content of silver was 0.0220 mass %, i.e. 220 p.p.m.