3,3`-Dithiobispropanoic acid bis(N-hydroxysucciniMde ester) synthesis
- Product Name:3,3`-Dithiobispropanoic acid bis(N-hydroxysucciniMde ester)
- CAS Number:57757-57-0
- Molecular formula:C14H16N2O8S2
- Molecular Weight:404.42
6066-82-6
1119-62-6
57757-57-0
General procedure for the synthesis of bis(N-hydroxysuccinimide ester) 3,3'-dithiobispropionic acid from 3,3'-dithiobispropionic acid and N-hydroxysuccinimide: To a solution of dichloromethane (20 mL) containing 3,3'-dithiobispropionic acid (1 g, 4.75 mmol) was added sequentially 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride ( WSC) (2.16 g, 10.5 mmol) and N-hydroxysuccinimide (1.21 g, 10.5 mmol). The reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, the solution was concentrated by vacuum to remove the solvent and the obtained residue was purified by silica column chromatography (eluent ratio ethyl acetate/hexane = 1:5) to give the final target product 3,3'-dithiodipropionic acid bis(N-hydroxybutanediimide ester) (1.63 g, 85% yield). The structure of the product was confirmed by 1H NMR (DMSO-d6, 400 MHz) and FAB mass spectrometry: 1H NMR δ 3.16 (m, 8H), 2.82 (s, 8H); FAB mass spectrometry (DMSO-d6) [(M+H)+] calculated value of 405, measured value 405.
6066-82-6
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1119-62-6
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57757-57-0
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Yield: 85%
Reaction Conditions:
with 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in dichloromethane at 20; for 2 h;
Steps:
2.3. Compound 2
To the solution of 3,3'-dithioldipropionic acid (1 g, 4.75 mmol) in dichloromethane (20 mL), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) (2.16 g, 10.5 mmol) and N-hydroxysuccinimide (1.21 g, 10.5 mmol) were added. The mixture was stirred for 2 h at room temperature. The solution was concentrated in vacuo, and the obtained residue was subjected to silica column chromatography (ethyl acetate/hexane = 1:5) to give the NHS ester 2 (1.63 g, 85%). 1H NMR (DMSO-d6, 400 MHz) δ 3.16 (m, 8H), 2.82 (s, 8H). FAB (DMSO-d6) [(M+H)+] calcd 405, found 405.
References:
Tanaka, Kazuo;Kitamura, Narufumi;Chujo, Yoshiki [Bioorganic and Medicinal Chemistry,2012,vol. 20,# 1,p. 96 - 100] Location in patent:experimental part
74124-79-1
481 suppliers
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1119-62-6
229 suppliers
$5.00/5g
57757-57-0
176 suppliers
$56.00/100MG
6066-82-6
811 suppliers
$5.00/10g
107-96-0
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57757-57-0
176 suppliers
$56.00/100MG