4-nitro-L-phenylalanine dipeptide derivatives as well as preparation method and applications thereof
A technology of nitrophenylalanine dipeptide and nitrophenylalanine methyl ester, which is applied in the field of dipeptide derivatives, can solve problems such as large side effects and unsatisfactory treatment effects, and achieve convenient post-processing, low cost, The effect of mild reaction conditions
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Embodiment 1
[0036] The preparation of embodiment 1, L-p-nitrophenylalanine (compound III)
[0037] L-p-nitrophenylalanine can be purchased directly from the market, or can be prepared by itself. The present invention adopts the following improved method to prepare: in a round-bottomed flask, add a mixed solution of concentrated nitric acid and concentrated sulfuric acid with a volume ratio of 1:1.3, cool to a temperature of 0 DEG C in an ice bath, and slowly add L-phenylalanine in batches , the molar ratio of L-phenylalanine and concentrated nitric acid is 1: 1.3, and the addition is completed, and the temperature is 0 ℃ of stirring for 60 minutes, then warming up to room temperature for 60 minutes, after the reaction is completed, add a small amount of ice-water mixture, stir Cool to 0°C, adjust pH to 6 with concentrated ammonia water under ice bath condition, separate out a large amount of precipitation, refrigerate, filter, wash the filter cake successively with ice water and ethanol, ...
Embodiment 2
[0062] The preparation of embodiment 2, L-p-nitrophenylalanine methyl ester hydrochloride (compound IV)
[0063] L-p-nitrophenylalanine methyl ester hydrochloride can be purchased directly from the market, and can also be prepared by itself. The present invention adopts the following improved method to prepare: adding anhydrous methanol to a round-bottomed flask, cooling to a temperature of 0 °C in an ice bath, slowly adding thionyl chloride, after the addition, stirring and reacting at a temperature of 0 °C for 20 minutes, adding compound III in batches That is, L-p-nitrophenylalanine, stir until the raw material gradually dissolves into a white turbid liquid, then heat up to 70 ° C and stir the reaction, it can be seen that the raw material is quickly dissolved into a yellow clear liquid, and the reaction is monitored by thin layer chromatography (TLC). Process; after the reaction of L-p-nitrophenylalanine is completed, rotary distillation under reduced pressure is carried o...
Embodiment 3
[0067] Embodiment 3, L-p-nitrophenylalanine dipeptide derivative Fmoc-AA-Phe (p-NO 2 )-OMe Preparation
[0068] General method: Dissolve Fmoc-AA-OH (20mmol) in 10mL of anhydrous THF, add HOBt (24mmol), DIC (24mmol) and DIPEA (20mmol) under ice bath and stirring, after the addition is complete, stir the reaction under ice bath for 30 ~60 minutes, monitor the generation of activated ester by TLC method; Dissolve compound IV, i.e., L-p-nitrophenylalanine methyl ester hydrochloride (20mmol) in anhydrous THF 15mL, add DIPEA (30mmol), stir, Standby; mix the above two solutions, stir and react at room temperature, and monitor the reaction process by TLC method; after the reaction is completed, remove THF by distillation under reduced pressure, add 150 mL of water to the residual liquid, extract with 150 mL of ethyl acetate, and collect the water layer respectively and the organic layer, and the aqueous layer was extracted with 80 mL of ethyl acetate, and all the organic layers were ...
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