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Synlett 2016; 27(19): 2685-2688
DOI: 10.1055/s-0036-1588300
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis of a Novel Rhizobitoxine-Like Triazole-Containing Amino Acid

Thibaut Boibessot
a   Université de Nîmes, EA7352 CHROME, Rue du Dr G. Salan, 30021 Nîmes Cedex 1, France   eMail: patrick.meffre@unimes.fr
,
David Bénimèlis
a   Université de Nîmes, EA7352 CHROME, Rue du Dr G. Salan, 30021 Nîmes Cedex 1, France   eMail: patrick.meffre@unimes.fr
,
Marion Jean
b   Aix Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille, France
,
Zohra Benfodda
a   Université de Nîmes, EA7352 CHROME, Rue du Dr G. Salan, 30021 Nîmes Cedex 1, France   eMail: patrick.meffre@unimes.fr
,
Patrick Meffre*
a   Université de Nîmes, EA7352 CHROME, Rue du Dr G. Salan, 30021 Nîmes Cedex 1, France   eMail: patrick.meffre@unimes.fr
› Institutsangaben
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Publikationsverlauf

Received: 10. Juni 2016

Accepted after revision: 05. August 2016

Publikationsdatum:
18. August 2016 (online)

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Abstract

The synthesis of the four stereoisomers of a new 1,2,3-triazole analogue of rhizobitoxine from serine is described. The key step is a Huisgen 1,3-dipolar cycloaddition on an ethynylglycine synthon.

Key word

rhizobitoxine - triazole amino acid - Huisgen cycloaddition - ethynylglycine synthon - chiral HPLC

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588300.
  • Supporting Information
 

  • References and Notes

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  • 44 General Synthetic Procedure for Click-Chemistry Reaction for the Synthesis of 2 (S)-Methyl 2-[(tert-Butoxycarbonyl)amino]-3-(4-{(S)-1-[(tert-butoxycarbonyl)amino]-2-hydroxyethyl}-1H-1,2,3-triazol-1-yl)propanoate [(1S,2S)-2, (Scheme 4, Path a] To a solution of (2S, 4S)-11 (0.337 g, 0.72 mmol) in MeOH (5 mL) was added PTSA·H2O (0.137 g, 0.72 mmol). The reaction mixture was stirred for 2 h at room temperature and sat. aq NaHCO3 solution (40 mL) was poured into the solution. The aqueous solution was extracted with EtOAc (3 × 40 mL). The organic phases were combined, washed with sat. aq NaHCO3 solution (40 mL), sat. aq NaCl solution (40 mL), dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, EtOAc–PE = 0:100, increasing to 100:0, v/v) to give the desired compound (1S, 2S)-2 (0.053 g, 17%) as a white solid and recovered starting material (2S, 4S)-11 (0.184 g, 55%). Analytical Data Rf = 0.26 (EtOAc); mp 55–57 °C. 1H NMR (300 MHz, CDCl3): δ = 1.42 [s, 18 H, C(CH3)3], 2.89 (br s, 1 H, OH), 3.79 (s, 3 H, CO2CH3), 3.84–3.87, 4.10–4.12 (2 m, 2 H, CH2O), 4.70–4.86 (m, 4 H, 2 CH, CH2N), 5.43 (br s, 1 H, NH), 5.59 (br s, 1 H, NH), 7.57 (s, 1 H, CHtriazole). 13C NMR (75 MHz, CDCl3): δ = 28.4, 28.5 [2 s, 18 H, C(CH3)3], 48.2 (CH), 51.5 (CH2N), 53.4 (CO2CH3), 53.9 (CH), 65.0 (CH2O), 80.1 [C(CH3)3], 81.0 [C(CH3)3], 123.9 (CHtriazole), 147.1 (Ctriazole), 155.2 (NCO2), 155.8 (NCO2), 169.5 (CO2CH3). [α]D 20 +49.9 (c 0.91, CHCl3). HRMS (ES+): m/z [M + H]+ calcd for C18H32N5O7: 430.2302; found: 430.2303. HPLC: purity = 99.6%, t R = 12.43 min. IR: 3358, 2362, 2338, 1742, 1683 cm–1. Nitrogen inversion in the oxazolidine ring or slow interconversion of both amide or carbamate conformers of compounds 4, 11, and 2 causes considerable line broadening and duplication of signals in the 1H NMR and 13C NMR spectra (see Supporting Information). General Synthetic Procedure for Click-Chemistry Reaction for the Synthesis of 2 (S)-Methyl 2-[(tert-Butoxycarbonyl)amino]-3-(4-{(S)-1-[(tert-butoxycarbonyl)amino]-2-hydroxyethyl}-1H-1,2,3-triazol-1-yl)propanoate [(1S,2S)-2, Scheme 4, Path b) Azide 3 (0.420 g, 1.72 mmol) and alkyne 12 (0.318 g, 1.72 mmol) were dissolved in a mixture of t-BuOH–H2O (10 mL, 1:1, v/v). Sodium l-asborbate (0.068 g, 20 mol%) and CuSO4·5H2O (0.041 g, 10 mol%) were added. The reaction mixture was stirred at room temperature for 24 h, the solution was concentrated under vacuum and diluted with H2O (70 mL). The aqueous phase was extracted with EtOAc (3 × 50 mL). The organic phases were combined, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, EtOAc–PE = 0:100, increasing to 100:0, v/v) to give the desired compound (1S,2S)-2 as a white solid (0.480 g, 65% yield). The compound exhibited the same analytical properties as described above. See Supporting Information for the characterization data of other products