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Chemical Structure| 341498-08-6 Chemical Structure| 341498-08-6

Structure of SPP
CAS No.: 341498-08-6

Chemical Structure| 341498-08-6

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Synonyms: N-succinimidyl 4-(2-pyridyldithio)pentanoate

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Product Details of [ 341498-08-6 ]

CAS No. :341498-08-6
Formula : C14H16N2O4S2
M.W : 340.42
SMILES Code : CC(SSC1=NC=CC=C1)CCC(ON2C(CCC2=O)=O)=O
Synonyms :
N-succinimidyl 4-(2-pyridyldithio)pentanoate
English Name :2,5-Dioxopyrrolidin-1-yl 4-(pyridin-2-yldisulfaneyl)pentanoate
MDL No. :MFCD20230233
InChI Key :GTBCXYYVWHFQRS-UHFFFAOYSA-N
Pubchem ID :11588139

Safety of [ 341498-08-6 ]

Application In Synthesis of [ 341498-08-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 341498-08-6 ]

[ 341498-08-6 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 452072-22-9 ]
  • [ 6066-82-6 ]
  • [ 341498-08-6 ]
YieldReaction ConditionsOperation in experiment
45% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 2h;
45% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2h; 2b Preparation of N-succinimidyl ester of 4-(2-pyridyldithio)-pentanoic acid (SPP, 7): A solution of 4-(2-pyridyldithio)-pentanoic acid (5, 30 g, 123 mmol) in methylene chloride (525 mL) was treated with N-hydroxysuccinimide(14.3 g, 124 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide.HCl (31.8 g, 165 mmol). The contents werestirred at room temperature for 2 hours after which 750 mL of ethyl acetate was added. The solution was washed with0.5% aqueous acetic acid (3 x 350 mL) and once with 150 mL of saturated aqueous sodium chloride. The organic layerwas dried over anhydrous sodium sulfate, filtered, and the solvent was removed under vacuum by rotary evaporation.The residue was taken up in a minimum volume of ethyl acetate and loaded on a 6.25 x 20 cm silica column, slurrypacked in 1:1 hexanes:ethyl acetate. The column was eluted with 1:1 hexanes:ethyl acetate. Fractions containing theproduct were combined and solvent was removed by rotary evaporation. The resulting oil (31 g) was taken up in a minimum volume of warm reagent grade ethanol and magnetically stirred as 350 mL of ethyl ether was added, followedby 100 mL of hexanes. The resulting precipitate was collected by vacuum filtration and dried in a vacuum oven at 30degrees C for 12 hours, giving 18.7 g of SPP (7) as a white solid(18.7 g, 45 % yield). 1H NMR (CDCL3) δ 1.39 (d, 3 H),2.0 (t, 3H), 2.56-3.4 (m, 7 H), 6.8-7.2 (m, 1 H), 7.6-7.8 (m, 2H), 8.4-8.6 (d, 1H). Elemental analysis: Calculated: %C 49.4,%H 4.70, %N 8.20, %S 18.80. Found: %C 49.3 %H 4.68, %N 8.18, %S 18.94.
23.5% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl acetamide at 20℃; 5 [00344] Synthesis of 2,5-dioxopyrrolidin-l-yl 4-(pyridin-2-yldisulfaneyl)pentanoate (linker I) To a solution of 4-(pyridin-2-yldisulfaneyl) pentanoic acid (24 mg, 0.1 mmol) and NHS (14 mg, 0.12 mmol) in DMA is added EDC (HC1 salt, 61 mg, 0.32 mmol). The solution is stirred at room temperature overnight. After filtration, the filtrate is concentrated and purified by column (MeOH/DCM = 0% to 10%) to obtain 2,5-dioxopyrrolidin-l-yl 4- (pyridin-2-yldisulfaneyl)pentanoate as white solid (8 mg, 23.5%). (MS: [M+l]+ 341.1).
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl acetamide at 25℃; for 1h; 23.1.1 Procedure for preparation of compound 3 To a solution of compound 1 (0.025 g, 102.73 umol, 1 eq.) in DMA (1 mL) was added EDCI (21.66 mg, 113.01 umol, 1.1 eq.) and compound 2 (13.01 mg, 113.01 umol, 1.1 eq.). The reaction mixture was stirred at 25 °C for 1 h. LC-MS showed a peak with desired m/z (341 [M+H+]) and the crude product was used directly in the next step without further purification.

 

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