반응 #11832

반응 방정식

ethyl acetate

N-(2,6-Diisopropylphenyl)-N′-(2-hydroxy-5-methylphenyl)-oxalamide

1-adamantol

H2SO4

→

solid

수율 48.4%

N-(2,6-diisopropylphenyl)-N′-(2-hydroxy-3-(adamant-1-yl)-5-methylphenyl)-oxalamide

수율 48.4%

용매

—

hexanes

CH2Cl2

반응 조건

후처리

1. 1
   기타according to the synthesis method
2. 2
   기타forming a suspension
3. 3
   workup.ADDITIONAfter addition of the acid
4. 4
   기타At this point, the solvent was removed under reduced pressure
5. 5
   workup.DISSOLUTIONthe resulting solids were redissolved in ethyl acetate (100 ml)
6. 6
   세척The resulting solution was then washed with saturated NaHCO3 (3×50 ml, gas is evolved), and brine
7. 7
   건조dried over MgSO4
8. 8
   기타The solvent was removed under reduced pressure
9. 9
   기타the resulting solid was purified via column chromatography

실험 절차

N-(2,6-Diisopropylphenyl)-N′-(2-hydroxy-5-methylphenyl)-oxalamide (5.59 g, 15.5 mmol, 1.0 eq), prepared according to the synthesis method described in Example 8, and 1-adamantol (2.83 g, 18.6 mmol, 1.2 eq) were dissolved in CH2Cl2 (150 ml), forming a suspension. To this suspension was then added concentrated H2SO4 (1 ml). After addition of the acid, the solids eventually went into solution. After stirring at room temperature for 24 hours, the TLC (9:1 hexanes:ethyl acetate, visualized by UV) showed that most of the starting material had gone to product. At this point, the solvent was removed under reduced pressure, and the resulting solids were redissolved in ethyl acetate (100 ml). The resulting solution was then washed with saturated NaHCO3 (3×50 ml, gas is evolved), and brine, then dried over MgSO4. The solvent was removed under reduced pressure, and the resulting solid was purified via column chromatography to give a product, light yellow solid (3.68 g, 7.5 mmol, 48%). 1H NMR (300 MHz, CDCl3) δ 9.51 (s, 1H), 8.77 (s, 1H), 7.84 (s, 1H), 7.37 (t, J=7.2 Hz 1H), 7.23 (d, J=7.5 Hz, 2H), 7.00 (d, J=2.1 Hz, 1H), 6.94 (d, J=1.8 Hz, 1H), 3.01 (septet, J=6.9, 2H), 2.29 (s, 3H), 2.18 (bs, 6H), 2.10 (bs, 3H), 1.80 (bs, 6H), 1.22 (d, J=6.9, 12H); 13C NMR (75 MHz, CDCl3) δ 158.3, 158.2, 146.2, 145.8, 140.6, 129.9, 129.2, 129.2, 126.8, 124.7, 123.8, 120.9, 40.7, 37.3, 37.1, 29.1, 29.0, 23.6, 20.8. Anal. Calcd for C31H40N2O3: C, 76.19; H, 8.25; N, 5.73. Found: C, 75.89; H, 8.42; N, 5.37.

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