A facile synthesis of per(poly)fluoroalkyl substituted α-amino acid derivatives

Qiao-Sheng Hu

Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

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Chang-Ming Hu,

Corresponding Author

Chang-Ming Hu

Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, ChinaSearch for more papers by this author

Qiao-Sheng Hu,

Qiao-Sheng Hu

Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

Search for more papers by this author

Chang-Ming Hu,

Corresponding Author

Chang-Ming Hu

Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, ChinaSearch for more papers by this author

First published: 27 August 2010

https://doi.org/10.1002/cjoc.19970150314

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Abstract

Initiated by CrCl₃/Fe redox couple, per(poly)fluoroalkyl iodides added to methyl α-acetylamino acrylate, giving β-per(poly)fluoroalkyl α-amino acid derivatives in good yields.

References

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5 Methyl α-acetylamino acrylate was prepared according to the literature: Kolar, A. J.; Olsen, R. K., Synthesis, 457 (1977).
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6 Typical procedure: 5 mmol of 2, 7.5 mmol of ClC₂F₄I (la), 1 mmol of CrCl₃.6H₂O (20%) and 7.5 mmol of Fe powder were mixed in 20 mL of MeOH under nitrogen. The mixture wan stirred and heated at 60–65°C for 6 h (monitored by TLC). After the reaction waa complete, the mixture was poured into 30 mL of ice water and extracted with Et₂O (3×20 mL). The combined organic layer WM washed with brine and dried (Na₂SO₄). Evaporation and flash chromatography gave 3a in 75% yield. 3a: m.p. 67–69°C. V_max: 3350, 1740, 1640 cm^−l. δ_H(CDCI₃, 60 MHz): 6.50(d, J=8.0 Hz, 1H, NH), 4.90(m, lH, -CH-N), 3.80(s, 3H, OCHs), 2.80(td, J=18.8 He, 2H, CF₂CH₂), 2.10(s, 3H, CH₃CO) ppm. δ_F(56.4 MHz, CDClS, CF₃CO₂H as standard): -6.0(s, 2F, CF₂CI), 35.0(br.r, 2F, CF₂CH₂) ppm. m/z: 280(M⁺ + 1), 248(M+-MeO), 178(M⁺-CO₂Me-COCH₂, 100). Anal. C₈H₁₀CIF₄NO₃. Calcd: C, 34.35; H, 3.58; N, 5.01; F, 27.19. Found: C, 34.81; H, 3.57; N, 4.97; F, 26.73.
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Volume15, Issue3

May 1997

Pages 286-288

A facile synthesis of per(poly)fluoroalkyl substituted α-amino acid derivatives

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A facile synthesis of per(poly)fluoroalkyl substituted α-amino acid derivatives

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