反应详情

A solution of compound 119 (0.4 g, 1.119 mmol) in dry ethanol (20 mL) was treated with thiophene-2-carboximidothioic acid methyl ester hydroiodide (0.63 g, 2.239 mmol) at room temperature and stirred for 24 h. The solvent was evaporated, diluted with sat. NaHCO3 solution (20 mL) and product was extracted into CH2Cl, (2×25 mL). The CH2Cl2 layer was washed with brine (20 mL) and dried (Na2SO4). The solvent was evaporated and crude material was purified by column chromatography on silica gel (2 M NH3 in methanol: CH2Cl2, 5:95) to obtain compound 120 (0.4 g, 60%) as a yellow solid in 2:3 ratio of cis-trans diastereomers. 1H NMR (DMSO-d6) δ 0.98-1.08 (m, 3H), 1.38-1.56 (m, 11H), 1.68-1.85 (m, 4H), 2.05-2.18 (m, 2H), 3.02-3.17 (m, 3H), 3.70-3.76 (m, 1H), 6.31 (brs, 2H), 6.62-6.67 (m, 1H), 6.96-7.01 (m, 1H), 7.09-7.11 (m, 1H), 7.22-7.30 (m, 2H), 7.60 (d, 1H, J=5.1 Hz), 7.70-7.72 (m, 1H), 10.59, 10.62 (2s, 1H); ESI-MS m/z (%): 467 (MH+, 100).

1. customThe solvent was evaporated
2. additiondiluted with sat. NaHCO3 solution (20 mL) and product
3. extractionwas extracted into CH2Cl, (2×25 mL)
4. washThe CH2Cl2 layer was washed with brine (20 mL)
5. dry with materialdried (Na2SO4)
6. customThe solvent was evaporated
7. customcrude material was purified by column chromatography on silica gel (2 M NH3 in methanol: CH2Cl2, 5:95)