Direct Synthesis of Z, Boc, Fmoc, Alloc[ddot] Derivatives of 5-Aminooxazoles Starting from Acylamino Acids and Chlorosulfonylcarbamates

References

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• 1990 . “ ENRAF-NONIUS Molecular Structure Determination Package ” . In MolEN Version , The Netherlands : Enraf-Nonius, Delft . C14H16N2O3: Mr = 260.30, monoclinic, P21/a, a = 11.985(3), b = 6.846(2), c = 17.286(4) Å, β = 102.83(3)°, V = 1383(1) Å-3, Z = 4, Dx = 1.250 Mg.m-3, λ (MoKα) = 0.71073å, μ = 0.832 cm-1, F(000) = 552, T = 294 K. The sample (0.22*0.25*0.25 mm) was studied on an automatic diffractometer CAD-4 ENRAF-NONIUS with graphite monochromatized MoKα radiation. The cell parameters were obtained by fitting a set of 25 high-theta reflections. The data collection (2max = 54°, scan ω/2; = 1, tmax = 60 s, range HKL: H 0,15 K 0,8 L -22,22, intensity controls without appreciable decay (0.2%) gives 3219 reflections from which 1888 were independent (Rint = 0.016) with I>4.0[sgrave](I). After Lorenz and polarization corrections the structure was solved with SIR-92 which revealed the non hydrogen atoms of the structure. After anisotropic refinement, all the hydrogen atoms are found with a Fourier Difference. The whole structure was refined by the full-matrix least-square techniques (use of F magnitude; x, y, z, βij for C, O and N atoms, x, y, z for H atoms; 220 variables and 1888 observations; w = 1/[sgrave](Fo)2=[[sgrave]2(I) + (0.04Fo 2)2]-1/2) with the resulting R = 0.045, Rw = 0.042 and Sw = 0.866 (residual δρ ≤ 0.17 eÅ-3). Atomic scattering factors from International Tables for X-ray Crystallography (International Tables for X-ray Crystallography 1974. Vol. IV. Birmingham: Kynoch Press. Present distributor D. Reidel, Dordrecht). All the calculations were performed on a Silicon Graphics Indy computer with the MOLEN package
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• The N-alkylation reaction of oxazolecarbamates (1 equiv.) was carried out with allyl bromide or trityl chloride (1,1 equiv.) in presence of 10 equiv. of potassium carbonate in dry acetone (2h, r.t.). Compound 12 was treated by 2.5 equiv of allyl bromide to gave the disubstituted derivative. Under the SN-redox conditions, a mixture of equimolar quantities of oxazolecarbamate and DIAD in THF was added to a solution of triphenylphosphine and allylic alcohol. N-substituted derivatives were purified by silica gel column chromatography
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• 1HNMR: 3.85 (d,2H,CH 2NH), 7.0 (s,2H, NH2, exch), 7.5, 7.9 (2m, 3+2H, ArH), 8.7 (t,1H,CH2NH). MS (FAB+): 179 (MH+)
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• 1906 . Chem. Ber. , 39 : 637 138.5°C, 1HNMR: 3.70–3.95 (m,4H, 2xCH 2NH+), 5.15 (m,2H,=CH2), 5.80 (m,1H,CH), 7.5, 7.9 (2m, 3+2H, ArH), 8.1, 8.80 (2t,2H,2xCH2NH). MS (FAB+): 219 (MH+)
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