![](/CAS/GIF/194357-64-7.gif)
2',6'-DiMethylcarbonylphenyl-10-sulfopropylacridiniuM-9-carboxylate 4'-NHS Ester synthesis
- Product Name:2',6'-DiMethylcarbonylphenyl-10-sulfopropylacridiniuM-9-carboxylate 4'-NHS Ester
- CAS Number:194357-64-7
- Molecular formula:C30H26N2O9S
- Molecular Weight:590.6
![1,3-Propane sultone](/CAS/GIF/1120-71-4.gif)
1120-71-4
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$13.00/5g
![2',6'-DiMethylcarbonylphenyl 9-Acridinecarboxylate 4'-NHS Ester](/CAS/GIF/115853-72-0.gif)
115853-72-0
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$1390.00/250mg
![2',6'-DiMethylcarbonylphenyl-10-sulfopropylacridiniuM-9-carboxylate 4'-NHS Ester](/CAS/GIF/194357-64-7.gif)
194357-64-7
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Yield:194357-64-7 56%
Reaction Conditions:
in 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 155; for 16 h;
Steps:
4
Example 4; [0081] N-Alkvation on a half- gram scale of 2>.6-dimethyl-4'-N- succinimidyloxycarbonylphenyl acridine-9-carboxylate with propane sultone in [BMIMl[PFoI: Synthesis of 26'-dimethyl-4'-N-succinimidyloxycarbonylphenyl-10- sulfopropylacridinium-9-carboxylate (NSP-DMAE-NHS).; [0082] To an 8 dram vial was added 0.50 g (1.07 mmol) of 2',6-dimethyl-4'-N- succinimidyloxycarbonylphenyl acridine-9-carboxylate, 5 g (17.6 mmol) of l-butyl-3- methylimidazolium hexafluorophosphate [BMIM]PF6] (Fluka) and 1.31 g (10.7 mmol) of distilled 1,3-propanesultone under nitrogen. This sealed vial was heated to 1550C for 16 hours. Then the reaction mixture was cooled to 4O0C and added drop wise to 100 ml of ethyl acetate with stirring which gave a yellow precipitate. The mixture was stirred at room temperature for 2 hours and filtered. The filter cake was washed with ethyl acetate (30 ml x 2) and dried under high vacuum which gave 0.753 of a yellow solid. The crude product was purified by preparative HPLC on Waters system using an YMC, C 18 column, 50 x 500 mm, with a solvent flow rate of 60 ml/minute, UV detection at 260 nm, elution being performed with 35%B over 50 minutes (A: water/0.05%TFA; B: acetonitrile/0.05%TFA). After lyophilization of the HPLC fractions, the desired product NSP-DMAE-NHS ester, 0.356 g (56% yield), was obtained as a yellow powder.
References:
WO2009/67417,2009,A1 Location in patent:Page/Page column 28