Preparation method and application of MMAF chiral isomer
A technology of chiral isomers and enantiomers, which is applied in the field of preparation of chiral compounds to achieve the effects of high yield, mild reaction conditions and low cost
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Embodiment 1
[0046] Embodiment 1, the preparation of compound 8
[0047] N-Boc-L-proline aldehyde (5 g) was dissolved in 100 ml of dichloromethane, methyl acrylate 6 (10 g) was added under nitrogen protection, and stirred at room temperature for 7 days until the reaction was complete. The dichloromethane solvent was removed by rotary evaporation to obtain 7 g of methyl ester compound 7 (2S, 3'R and 2S, 3'S) isomer mixture.
[0048] The sample was loaded by wet method, and the separation and developing solvent was n-hexane: ethyl acetate = 6: 1. After separation by silica gel column chromatography, 3 g of 2S, 3′S-methyl ester compound 8 was obtained.
Embodiment 2
[0049] Embodiment 2, the preparation of compound 9
[0050] Compound 8 (3 g) was dissolved in 100 ml of ethyl acetate, 0.15 g of palladium carbon was added, and after vacuuming, it was replaced by hydrogen gas three times, and reacted overnight (about 16 hours) at room temperature and normal pressure. After the reaction was completed, diatomaceous earth was added to filter, and ethyl acetate was removed by rotary evaporation to obtain 1.5 g of a mixture 9 containing two chiral isomers. The mixture 9 contained a chiral configuration of 2S, 3'S, 2 Compound 9a with 'R and compound 9b with chiral configuration 2S, 3'S, 2'S.
Embodiment 3
[0051] Embodiment 3, the preparation of compound 10
[0052] 1.5 g of compound 9 was added into a 100 ml three-necked flask, and under nitrogen protection, 0.2 g of dried molecular sieves and 30 ml of anhydrous dichloromethane were added. Add 1,8-bisdimethylaminonaphthalene (2 g) and trimethyloxonium tetrafluoroboric acid (0.8 g) successively, and react at room temperature for 28 hours. The solid matter was removed by filtration, and the obtained reaction solution was loaded by a wet method. The developing solvent was n-hexane:ethyl acetate=15:1, and 1.1 g of solid was obtained.
[0053] The solid (0.5 g) was dissolved in 30 ml of tetrahydrofuran: water = 2:1 solution under nitrogen protection, and 10 ml of 5% LiOH solution was added when the temperature was about 0° C. under stirring. Raise the temperature and react at room temperature for 20 hours. After the reaction, remove THF by rotary evaporation, adjust the pH to 2 with 1M hydrochloric acid solution, extract 3 times wi...
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