Process for complete synthesizing quinamide of diji frog of high antimer pure nutural
A technology of quinamide and natural products of Rana chinensis, applied in the direction of organic chemistry and the like, can solve the problems of inconvenient operation, unstable intermediate products, etc., and achieve the effects of high reaction yield and simple operation and separation
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Embodiment 1
[0046] The synthesis method of the negative optical rotation spina quinamide is as follows.
[0047] 1) Synthesis of 4-tert-butyldimethylsilyloxy-1-butanol 1: Add 1,4-butanediol (5.4g, 60mmol) to dissolved sodium hydride (2.4g, 60mmol) at 0°C ) in tetrahydrofuran (150 mL), then raised to room temperature and stirred for 45 min, gas was generated and a large amount of white precipitate was produced. Add tert-butyldimethylsilyl chloride (9.0 g, 60 mmol) at 0° C. and stir vigorously for 45 min. Diethyl ether (100 mL) was added, and the organic phase was washed with 10% potassium carbonate solution and brine, dried over anhydrous sodium sulfate, and concentrated to obtain an oily substance. Purification by silica gel column chromatography (ethyl acetate:petroleum ether=1:1) gave Compound 1 as a colorless oil with a yield of 97%.
[0048] 2) Synthesis of 4-bromo-1-tert-butyldimethylsilyloxy-butane 2: Under the protection of nitrogen, elemental bromine (2.7mL, 52.5mmol) was added ...
Embodiment 2
[0065] 1) Synthesis of 4-tert-butyldimethylsilyloxy-1-butanol 1: The operation process of compound 1 is the same as that of Example 1. 1,4-butanediol (2.7g, 30mmol) was added to a tetrahydrofuran solution (100mL) dissolved with sodium hydride (1.8g, 45mmol) at 0°C, then raised to room temperature and stirred for 45min, gas was generated and a large amount of of white precipitate. Add tert-butyldimethylsilyl chloride (4.5 g, 30 mmol) at 0°C and stir vigorously for 45 min. Diethyl ether (100 mL) was added, and the organic phase was washed with 10% potassium carbonate solution and brine, dried over anhydrous sodium sulfate, and concentrated to obtain an oily substance. Purification by silica gel column chromatography (ethyl acetate:petroleum ether=1:1) gave Compound 1 as a colorless oil with a yield of 90%.
[0066] 2) Synthesis of 4-bromo-1-tert-butyldimethylsilyloxy-butane 2: The preparation of compound 2 is the same as in Example 1. Under nitrogen protection, elemental brom...
Embodiment 3
[0082] 1) Synthesis of 4-tert-butyldimethylsilyloxy-1-butanol 1: The preparation of compound 1 is the same as in Example 1. The operation process of Compound 1 is the same as in Example 1. 1,4-Butanediol (5.4g, 60mmol) was added to a tetrahydrofuran solution (150mL) dissolved with sodium hydride (2.9g, 72mmol) at 0°C, then raised to room temperature and stirred for 45min, gas was generated and a large amount of of white precipitate. tert-Butyldimethylsilyl chloride (4.5 g, 30 mmol) was added at 0 °C and stirred vigorously for 1 h. Diethyl ether (100 mL) was added, and the organic phase was washed with 10% potassium carbonate solution and brine, dried over anhydrous sodium sulfate, and concentrated to obtain an oily substance. Purification by silica gel column chromatography (ethyl acetate:petroleum ether=1:1) gave Compound 1 as a colorless oil with a yield of 93%.
[0083] 2) Compound 1→Compound 2: The preparation of Compound 2 is the same as in Example 1. Under nitrogen p...
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