反应详情

4-Chloro-4-methyl-3-nitrosopentane (0.52 g, 3.5 mmol, Example 27(A)) was added to a mixture of the hydrochloride title product of step B above (0.62 g, 1.5 mmol) and diisopropylethylamine (0.45 g, 3.5 mmol) in acetonitrile (10 mL), and the mixture was stirred at room temperature for 12 hrs. Acetonitrile was removed on a rotary evaporator and the thick oil obtained was basified with potassium carbonate solution. The light green oil obtained was extracted with ethyl acetate and dried (Na2 SO4). Ethyl acetate was removed on a rotary evaporator and the oil obtained was purified by column chromatography (silica gel, ethyl acetate:hexane, 6:4). Fractions containing the product were collected and evaporated to give a colorless oil, which was dried under vacuum to afford a foamy solid. The solid obtained was dissolved in acetonitrile and left at room temperature for 2 hrs. The solid that formed was filtered and recrystallized from acetonitrile. Yield: 0.32 g (47%). mp. 153°-154° C. 1HNMR (DMSO): δ 0.86, 0.96, 1.11, and 1.35 [m, 22H, C(CH3)2, CH2CH3 and CH2 CH2CH2CH3)], 2.15 (m, 4H, CH2CH2CH2 CH3 and CH2CH3), 2.30 (m, 2H, HNCH2CHOH), 3.80 (m, 1H, CHO), 4.5 (m, 2H, CHOHCH2N<), 7.14 and 7.56 (s, 2H, imiH), 10.35 (s, 1H, NOH), and 10.37 (s, 1H, NOH). MS:(M+H)+ =456 Anal. Calcd. for C20H37N7O5 : C, 52.71; H, 8.19; N, 21.53. Found: C, 52.94; H, 8.26; N, 21.63.

1. customAcetonitrile was removed on a rotary evaporator
2. customthe thick oil obtained
3. customThe light green oil obtained
4. extractionwas extracted with ethyl acetate
5. customdried (Na2 SO4)
6. customEthyl acetate was removed on a rotary evaporator
7. customthe oil obtained
8. customwas purified by column chromatography (silica gel, ethyl acetate:hexane, 6:4)
9. additionFractions containing the product
10. customwere collected
11. customevaporated
12. customto give a colorless oil, which
13. customwas dried under vacuum
14. customto afford a foamy solid
15. customThe solid obtained
16. waitleft at room temperature for 2 hrs
17. customThe solid that formed
18. filtrationwas filtered
19. customrecrystallized from acetonitrile