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Chemical Structure| 160580-70-1 Chemical Structure| 160580-70-1

Structure of PDP-Pfp
CAS No.: 160580-70-1

Chemical Structure| 160580-70-1

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Product Details of [ 160580-70-1 ]

CAS No. :160580-70-1
Formula : C14H8F5NO2S2
M.W : 381.34
SMILES Code : O=C(OC1=C(F)C(F)=C(F)C(F)=C1F)CCSSC2=NC=CC=C2
English Name :Perfluorophenyl 3-(pyridin-2-yldisulfaneyl)propanoate
MDL No. :MFCD28556889

Safety of [ 160580-70-1 ]

Application In Synthesis of [ 160580-70-1 ]

* 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 [ 160580-70-1 ]

[ 160580-70-1 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 68617-64-1 ]
  • [ 771-61-9 ]
  • [ 160580-70-1 ]
YieldReaction ConditionsOperation in experiment
66.1% With dicyclohexyl-carbodiimide In dichloromethane at 20℃; Inert atmosphere; 1-3-1 1-3-1. Synthesis of 3-(2-pyridyldithio)propionic acid pentafluorophenyl ester (PPDP) PDPA (5.34 g, 2.04 mmol), PFP (5.41 g, 6.73 mmol), and DCC (6.15 g, 6.77 mmol) were added to DCM (300 mL), and the reaction mixture was stirred overnight at room temperature under an Ar atmosphere. The reaction was terminated when the PDPA spot disappeared by TLC. The reaction solution was filtered to remove the by-product dicyclohexylurea, and the solvent was removed under reduced pressure using a rotary evaporator, yielding a pale yellow oil. This was dissolved in a small amount of solvent (AcOEt/Hexane = 1/1, v/v) and subjected to silica gel column chromatography (AcOEt/Hexane = 1/4, v/v) to isolate the peak believed to be the target product. The solvent was removed under reduced pressure using a rotary evaporator, and the resulting white solid was dried under reduced pressure at room temperature. The synthesis of PPDPwas confirmed by 1H NMR measurement. The yield was 2.93 g, a 66.1% yield.
64% With dicyclohexyl-carbodiimide In dichloromethane for 17h; Ambient temperature;
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 51h; Inert atmosphere;
  • 2
  • [ 6038-19-3 ]
  • [ 160580-70-1 ]
  • [ 3110305-52-4 ]
YieldReaction ConditionsOperation in experiment
55.9% With triethylamine In dichloromethane 1-3-2 1-3-2. Synthesis of PDTL(1a) from PPDP PPDP (0.41 g, 1.08 mmol) and DL-homocysteine thiolactone hydrochloride (0.166 g, 1.08 mmol) were added to DCM (20 mL). TEA (0.15 mL, 1.08 mmol) was then dripped over 15 minutes and stirred overnight. After the reaction, the solvent was distilled using a rotary evaporator and separated by silica gel column chromatography (EtOAc/Hexane = 1/1, v/v). After that, the peaks that seem to be the target were separated, the solvent was distilled under reduced pressure using a rotary evaporator, and the resulting material was depressurized and dried at room temperature to obtain a white solid. The synthesis of PDTL(1a) was confirmed by1H NMR measurement. The 1H NMR spectra of PDTL(1a) are shown in Figure 4. (Some ethyl acetate remains.) The yield was 0.190 g and the yield was 55.9%.
 

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