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Boc-Phe-Phe-OH

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Boc-Phe-Phe-OH Basic information

Product Name:
Boc-Phe-Phe-OH
Synonyms:
  • BOC-PHE-PHE-OH
  • BOC-L-DIPHENYLALANINE
  • Boc-L-Phenylalanyl-phenylalanine
  • N-Boc-L-phenylalanyl-L-phenylalanine, 95%
  • (S)-2-((S)-2-((tert-Butoxycarbonyl)aMino)-3-phenylpropanaMido)-3-phenylpropanoic acid
  • Boc-FF-OH
  • Boc-L-Phe-L-Phe-OH
  • (tert-butoxycarbonyl)-L-phenylalanyl-L-phenylalanine
CAS:
13122-90-2
MF:
C23H28N2O5
MW:
412.48
Mol File:
13122-90-2.mol
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Boc-Phe-Phe-OH Chemical Properties

Melting point:
72-75 °C
Boiling point:
660.3±55.0 °C(Predicted)
Density 
1.194±0.06 g/cm3(Predicted)
storage temp. 
Sealed in dry,2-8°C
form 
Solid
pka
3.53±0.10(Predicted)
Appearance
White to off-white Solid
CAS DataBase Reference
13122-90-2
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Boc-Phe-Phe-OH Usage And Synthesis

Synthesis

13122-89-9

13122-90-2

General procedure for the synthesis of Boc-L-phenylalanyl-phenylalanine from methyl (tert-butoxycarbonyl)phenylpropionyl-phenylpropionate: to a solution of methanol (20 ml) containing methyl 2-(2-((tert-butoxycarbonyl)amino)-3-phenylpropionamido)-3-phenylpropionate (2.0 g, 4.69 mmol), sodium hydroxide (0.38 g, 9.38 mmol) in water (10 ml) solution and the reaction temperature was maintained at 25-30°C. The reaction mixture was stirred at the same temperature for 1 hour. After completion of the reaction, methanol was removed by evaporation and the remaining aqueous layer was acidified with citric acid solution until the solid precipitated. The solid product was collected by filtration and dried to give Boc-L-phenylalanyl-phenylalanine as a white solid (1.89 g, 98% yield); ESI-MS: 413.2 (M + H).

References

[1] Patent: WO2016/181408, 2016, A2. Location in patent: Page/Page column 32
[2] Chemical Communications, 2016, vol. 52, # 28, p. 5045 - 5048
[3] Journal of the American Chemical Society, 2016, vol. 138, # 38, p. 12387 - 12394
[4] European Journal of Medicinal Chemistry, 1992, vol. 27, # 3, p. 179 - 186
[5] Angewandte Chemie - International Edition, 2017, vol. 56, # 43, p. 13288 - 13292

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