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68949141369
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note
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Conformations of N-benzylacetamide, 2-methyl-4-phenyl-1,3-oxazole and 2-methyl-4-phenyl-4,5-dihydro-1,3-oxazole were optimized using the MMFFs force field with a distance-dependent dielectric of 4r. For 2-methyl-4-phenyl-4,5-dihydro-1,3-oxazole, two conformations were found which differed in ring pucker; the lower-energy conformation was used for the overlay shown in Figure 2. Molecules were superimposed by minimizing RMSD between the methyl carbon; the N, C, and O of the heterocycle or amide; and the phenyl ring centroid.
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6
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68949151467
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note
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Intermediate I was extracted into basic aqueous layer, while diamide by-product was washed away with EtOAc. Aqueous portion was then acidified and intermediate I was extracted into EtOAc. Since unreacted diacid starting material has higher aqueous solubility, this workup gave essentially pure intermediate I.
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7
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0034689867
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Phillips A.J., Uto Y., Wipf P., Reno M.J., and Williams D.R. Org. Lett. 2 (2000) 1165
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Phillips, A.J.1
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Williams, D.R.5
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9
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68949140485
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note
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v1.7 channels.
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10
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4043083603
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Felix J.P., Williams B.S., Priest B.T., Brochu R.M., Dick I.E., Warren V.A., Yan L., Slaughter R.S., Kaczorowski G.J., Smith M.L., and Garcia M.L. Assay Drug Dev. Tech. 2 (2004) 260
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Felix, J.P.1
Williams, B.S.2
Priest, B.T.3
Brochu, R.M.4
Dick, I.E.5
Warren, V.A.6
Yan, L.7
Slaughter, R.S.8
Kaczorowski, G.J.9
Smith, M.L.10
Garcia, M.L.11
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12
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68949160557
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note
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Chiral OJ column, 15 × 250 mm; mobile phase: 12% IPA, 88% heptane; flow rate: 9 ml/min. Retention time for the four isomers: 17, 23, 31, 37 min.
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13
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0027933374
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Chaplan S.R., Bach F.W., Pogrel J.W., Chung J.M., and Yaksh T.L. J. Neurosci. Methods 53 (1994) 55
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