Microwave-assisted ring-opening of activated aziridines with resin-bound amines

Journal of Organic Chemistry

Volumn 73, Issue 9, 2008, Pages 3566-3569

  Crestey, François ^a   Witt, Matthias ^b   Frydenvang, Karla ^a   Stærk, Dan ^a   Jaroszewski, Jerzy W ^a   Franzyk, Henrik ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b BRUKER DALTONIK GMBH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; MICROWAVE IRRADIATION; OPTIMIZATION; ORGANIC SOLVENTS; RESINS; SYNTHESIS (CHEMICAL);

AZIRIDINES; SOLID PHASE SYNTHESIS (SPS);

AMIDES;

AMINE; AZIRIDINE; GLYCINE; PROLINE; RESIN;

ARTICLE; CHEMICAL REACTION; MICROWAVE RADIATION; RING OPENING;

AMINES; AZIRIDINES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; MICROWAVES; MOLECULAR STRUCTURE;

EID: 43449125001     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702612u     Document Type: Article

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30. D) of 2e was opposite to that of other aziridine building blocks with similar stereochemistry, but crystallization and subsequent X-ray structure determination confirmed unequivocally its stereochemistry. For details of crystallographic data of compounds 2c and 2e, see the Supporting Information.
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32. 2 (50:50. 2 x 3 mL for 30 min), and the resulting combined solutions were coevaporated with toluene in vacuo to give the desired compound 17a.
33. 1H NMR of the obtained crude material.
34. Compound 23 was isolated with a >85% yield and a 93% purity. Compound 24 was isolated with ∼70% yield and a 93% purity (∼30% of the starting material was recovered also).
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36. The mass spectra of all glycine derivatives (including regioisomers) were obtained by HPLC-MS analysis. In each case, a [M - 46] peak was detected, corresponding to the loss of the nitro group of the nosyl moiety.
37. The molecular ion peak in HPLC-MS of the unknown product with a retention time of 27.0 min (see Figure 1) was [M + H] = 179.
38. For details of identification of each compound, see the Supporting Information.
39. In contrast to other sulfonamide activating groups, the nosyl group may be removed under mild conditions compatible with SPS protocols; see: Olsen, C. A.; Witt, M.; Jaroszewski, J. W.; Franzyk, H. Synlett 2004, 473-476, and references cited herein.