N-Succinimidyl maleimidoacetate synthesis
- Product Name:N-Succinimidyl maleimidoacetate
- CAS Number:55750-61-3
- Molecular formula:C10H8N2O6
- Molecular Weight:252.18
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Yield: 116 g
Reaction Conditions:
with triethylamine in dichloromethane at 20; for 2 h;
Steps:
7 Example 7
Synthesis of succinimidyl N-maleimidyl acetate, a compound of formula (V) wherein X is 1.
To a 500 ml three-necked flask, N-maleimidyl acetic acid (94 g, 0.6 mol)And dichloromethane 300ml,Oxalyl chloride (90 g, 0.72 mol) was then added,The reaction was warmed to reflux, a large amount of gas was released.After 2h the reaction became clear,Concentrate to remove methylene chloride and excess oxalyl chloride,Addition of 200 ml of methylene chloride to remove the residual acid in one pass afforded crude N-maleimidoacetyl chloride.The crude product was dissolved in 200 ml of dichloromethane,Was added dropwise to N-hydroxysuccinimide (69 g, 0.6 mol)Triethylamine (80.8 g, 0.8 mol)Dissolved in 300 ml of dichloromethane,Ice water cooling control temperature does not exceed 20 , drip finished room temperature 2h.The reaction solution was washed with 200 ml of water to remove triethylamine hydrochloride,1N hydrochloric acid 100ml washing to remove excess triethylamine,200ml saturated salt water, washed and dried,Concentrated to dry off like white solid 137g,After recrystallization from a mixed solvent of ethyl acetate and petroleum ether, 116 g of a white solid was obtained,HPLC purity 98.7%, 76.7% yield.
References:
Suzhou Haofan Biological Technology Co., Ltd.;Lv Minjie;Zhang Haiyan;Wang Guichun;Sun Fangchao CN105037237, 2017, B Location in patent:Paragraph 0071-0074
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