CN107033033A - The synthetic method of hydroxytyrosine between a kind of N α fluorenylmethyloxycarbonyls - Google Patents

The synthetic method of hydroxytyrosine between a kind of N α fluorenylmethyloxycarbonyls Download PDF

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Publication number
CN107033033A
CN107033033A CN201610894973.3A CN201610894973A CN107033033A CN 107033033 A CN107033033 A CN 107033033A CN 201610894973 A CN201610894973 A CN 201610894973A CN 107033033 A CN107033033 A CN 107033033A
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synthetic method
extraction
ether
washing
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徐红岩
颜行
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Shanghai GL peptide Ltd
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Shanghai GL peptide Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C269/04—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from amines with formation of carbamate groups

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The present invention relates to a kind of synthetic method of hydroxytyrosine between N α fluorenylmethyloxycarbonyls.Mainly solve that cost present in existing synthetic method is high, heavy-polluted technical problem.Technical scheme is：The synthetic method of hydroxytyrosine between a kind of N α fluorenylmethyloxycarbonyls, including：1st, DL m-Tyrosines are dissolved in aqueous slkali, add ice-water bath after acetone, add fluorenes methoxy carbonyl acyl succinimide, regulation solution ph TLC tracks to reaction end；2nd, reaction solution through suction filtration, extraction, add ethyl acetate, it is acidified, layering, extraction, TLC detection product be extracted into completely in ethyl acetate phase, then through overpickling, washing and saturated common salt wash after anhydrous sodium sulfate drying stay overnight；Filtering and washing anhydrous sodium sulfate, then vacuum distillation solvent, plus petroleum ether stand to there is white opacity；3rd, product will be stood and is dissolved in aqueous slkali, add ether, acidified, layering, extraction, TLC detection products are extracted into ether phase completely, then post-treated vacuum distillation solvent, plus petroleum ether is to white opacity, you can separate out white solid product.

Description

A kind of synthetic method of N α-fluorenylmethyloxycarbonyl-hydroxytyrosines
Technical field
The present invention relates to a kind of synthetic method of tyrosine, more particularly to a kind of N α-fluorenylmethyloxycarbonyl-hydroxytyrosines Synthetic method.
Background technology
Between hydroxytyrosine be a kind of aromatic series polarity alpha amino acid containing phenolic hydroxyl group, a hydroxytyrosine is composition egg One kind in 20 kinds of amino acid of white matter, is the essential amino acid of mammal, and a hydroxytyrosine is a kind of white crystalline body Or crystalline powder, it is tasteless, formic acid is soluble in, water is insoluble in, insoluble in ethanol and the chemicals of ether.
Between the extensive use in pharmaceutical chemistry of hydroxytyrosine and its derivative, particularly apply in central nervous system On drug research, such as parkinsonism（Eur. J. Pharmacol. 1973, 21, 230–237）(J. Med. Chem. 1992,35,1410-1417), alzheimer's disease WO2004062625,2004), arthritis (WO 19961465,1999) (WO2005058884, 2005).Also medicine can be done for hyperthyroidism, or food additives.It is also a kind of important simultaneously Biochemical reagents, be synthesis polypeptide parahormone, antibiotic, the primary raw material of the medicine such as L-3,4 dihydroxyphenylalanine.Agricultural sciences is widely used in grind Study carefully, also make beverage additive and prepare artificial insect's feed.
The synthetic method of current N α-fluorenylmethyloxycarbonyl-hydroxytyrosines is main using DMF, TEA as primary solvent, performance High for cost, pollution is big, is unfavorable for the big production of scale in the case of the unprecedented attaching importance to environmental protection of current governmental.
The content of the invention
It is an object of the invention to provide a kind of synthetic method of N α-fluorenylmethyloxycarbonyl-hydroxytyrosines, mainly solve existing Have that cost present in synthetic method is high, heavy-polluted technical problem.
The technical scheme is that：A kind of synthetic method of N α-fluorenylmethyloxycarbonyl-hydroxytyrosines, including it is following Step：
A, by DL- m-Tyrosines（DL-M-Tyrosine）Aqueous slkali is dissolved in, ice-water bath after acetone is added and is cooled to 0 DEG C, addition Fluorenes methoxy carbonyl acyl succinimide（FMOC-OSU）, solution pH value=8-9 is adjusted, TLC tracks to reaction end；
B, reaction solution add ethyl acetate through suction filtration, extraction, and acidified, layering, extraction, TLC detection products are extracted completely Anhydrous sodium sulfate drying is stayed overnight into ethyl acetate phase, then after the washing of overpickling, washing and saturated common salt；Filtering and washing nothing Then aqueous sodium persulfate, vacuum distillation solvent, plus petroleum ether stand to there is white opacity；
C, product will be stood it is dissolved in aqueous slkali, adds ether, acidified, layering, extraction, TLC detection products extract completely Get in ether phase, wash ether phase, saturated common salt washing ether phase, anhydrous sodium sulfate drying is stayed overnight；Filtering, washs anhydrous sulphur Sour sodium, vacuum distillation solvent, plus petroleum ether are to white opacity, you can separate out white solid product.
Reaction equation is as follows：
。
Aqueous slkali described in step a is one or both of sodium carbonate, sodium acid carbonate, sodium hydroxide mixed solution, excellent Select the sodium carbonate of mass percentage concentration 10% and the sodium acid carbonate mixed solution of mass percentage concentration 5%.Acidifying described in step b, c is used Solid citric acid for adjusting pH value=3-5；It is preferred that pH value=5.
The conventional abbreviation of some in the present invention has following meanings：
Fmoc- ：Fluorenylmethyloxycarbonyl
DL-M-TYROSINE :Between hydroxytyrosine
DL-M-Tyrosine：DL- m-Tyrosines
FMOC-OSU：Fluorenes methoxy carbonyl acyl succinimide.
The beneficial effects of the invention are as follows：Present invention mainly solves the conjunction of existing N α-fluorenylmethyloxycarbonyl-hydroxytyrosines Higher into method cost, pollution is high, is unfavorable for the technical problem largely produced, while obtained object can directly crystallize analysis Go out, without passing through high-efficient liquid phase chromatogram purification.
Brief description of the drawings
Fig. 1：Product nuclear magnetic resonance map of the present invention.
Fig. 2：Product high performance liquid chromatography of the present invention.
Fig. 3：Product infared spectrum of the present invention.
Fig. 4：Mass-spectrogram of the present invention.
Embodiment
Instrument needed for of the invention：
2F-I type ultraviolet analysis instrument for three purposed Shanghai Baoshan turns round and look at electric light equipment factory of village
85-1 type magnetic stirring apparatus Shanghai Zhi Wei Electrical Appliances Co., Ltd
Rotary Evaporators Shensheng Science ＆ Tech. Co., Ltd., Shanghai
The 400MHZ nuclear magnetic resonance spectrometer Bruker Biospin international of Bruker Ascend Avance III AG
WPS-1B numeral melting point instruments Shanghai Precision Scientific Apparatus Co., Ltd
SGW-1 spectrometers Shanghai Precision Scientific Apparatus Co., Ltd
LC-20AT high performance liquid chromatograph SHIMADU CORPORATIDN.
Embodiment
By DL-M-Tyrosine, 20 grams are suspended in the ML of 10% aqueous sodium carbonate of mass percentage concentration 100 and quality hundred In the ML of sodium bicarbonate aqueous solution 100 for dividing concentration 5%, after stirring, 200 ML acetone are added.Ice-water bath cools.In 0 FMOC-OSU is slowly added into DEG C 15 minutes.And with the aqueous sodium carbonate maintenance reaction liquid of mass percentage concentration 10% Between pH values 8-9.TLC（Solvent volume ratio chloroform:Methanol:Glacial acetic acid=90:8:2）Track reaction solution reaction eventually Point.
After reaction terminates, Buchner funnel suction filtration is used, solid detects no product by TLC, and solid abandons it.Liquid phase second Acetoacetic ester and petroleum ether 2:1 extraction 3 times, to extract the FMOC for not yet reacting clean.300ML ethyl acetate is subsequently added into, With solid citric acid acidizing PH value=3.Layering, extraction.Organic phase is stayed, is detected by TLC, product is extracted into acetic acid completely In ethyl ester phase.The aqueous citric acid solution washing ethyl acetate phase 3 times of 5% mass percentage concentration with to wash residual off to greatest extent OSU, then washes ethyl acetate phase, and saturated common salt washing is stayed overnight with anhydrous sodium sulfate drying, to remove lacking in ethyl acetate Measure moisture content.Anhydrous sodium sulfate is filtered, anhydrous sodium sulfate is washed with a small amount of ethyl acetate.45 DEG C of vacuum distillations（Vacuum- 0.09MPA）.Evaporate 1/2nd solvent, plus then petroleum ether stand to there is white opacity.
Stand product to be dissolved in the aqueous sodium carbonate of mass percentage concentration 10%, add 500ML ether, solid citric acid Acidizing PH value=5.Layering, extraction.It has been extracted into completely in ether phase by TLC detection products, has washed ether phase, saturation Salt washes ether phase, and anhydrous sodium sulfate drying is stayed overnight.
Filtering, a small amount of ether washs anhydrous sodium sulfate.Vacuum distillation at 45 DEG C（Vacuum -0.065MPA）.Plus petroleum ether is extremely White opacity, you can separate out white solid.Through filtering, 40 DEG C of oven for drying.Obtain 32 grams of FMOC-DL-M-TYROSINE. Rate 71%.HPLC：96.75%.57.1 DEG C of fusing point.Through nuclear magnetic resonance, infrared spectrum analysis meets product property.Reference picture 1,2,3.
Aqueous slkali contrast test is as follows in step a：
Experiment 1:
1.8 grams of DL-M-TYROSINE are dissolved in 1 N sodium hydrate aqueous solutions 18ML, add the acetone 18ML cryosels of equivalent Bath cooling.It is slowly added into FMOC-OSU in less than 0 DEG C, and with 1 N NAOH aqueous solution maintenance reaction liquid PH values 9.TLC （Solvent volume ratio chloroform:Methanol:Glacial acetic acid=90:8:2）System tracks response situation, and TLC observations are in Rf values 0.7 It is equipped with larger side reaction generation.Reaction in 2 hours terminates.
Experiment 2：
1.8 grams of DL-M-TYROSINE are dissolved in the aqueous sodium carbonate 18ML of mass percentage concentration 10%, add the acetone of equivalent 18ML is cooled with ice bath.It is slowly added into FMOC-OSU in less than 0 DEG C, and with the sodium bicarbonate aqueous solution of mass percentage concentration 10% Maintenance reaction liquid PH values 9.TLC（Solvent volume ratio chloroform:Methanol:Glacial acetic acid=90:8:2）System tracking reaction feelings Condition, TLC observation analysis has accessory substance generation.Reaction in 2.5 hours terminates.
Experiment 3：
1.8 grams of DL-M-TYROSINE are dissolved in the aqueous sodium carbonate of 10 ML mass percentage concentrations 10% and mass percentage concentration In 5% 10 ML sodium bicarbonate aqueous solutions, FMOC-OSU is slowly added into less than 0 DEG C, and with the carbon of mass percentage concentration 10% Acid sodium aqueous solution maintenance reaction liquid PH values 9.TLC（Solvent volume ratio chloroform:Methanol:Glacial acetic acid=90:8:2）System Response situation is tracked, the few accessory substance generations of TLC observation analysis, reaction in 2.5 hours terminates.
Buck used in the reaction for the experiment surface experiment 3 reacted by three of the above is best suitable for the product, produced Accessory substance it is minimum.Reference picture 4.
Acidizing PH value comparative selection experiment described in step b, c is as follows：
Experiment 4：（The selection of pH value during acidizing extraction）
With solid citric acid acidification reaction liquid pH value=3, ethyl acetate extraction, TLC（Solvent volume ratio chloroform:Methanol: Glacial acetic acid=90:8:2）System anlysis shows to be extracted into impurity in organic phase in the lump.
Experiment 5：
With solid citric acid acidification reaction liquid pH value=3, ether extraction, TLC（Solvent volume ratio chloroform:Methanol:Ice second Acid=90:8:2）System anlysis shows can be by a small amount of impurity extraction into organic phase.
Experiment 6；
With solid citric acid acidification reaction liquid pH value=5, ethyl acetate extraction, TLC（Solvent volume ratio chloroform:Methanol: Glacial acetic acid=90:8:2）A small amount of impurity can be extracted into organic phase by system anlysis surface in the lump.
Experiment 7：
With solid citric acid acidification reaction liquid PH value=5, ether extraction, TLC（Solvent volume ratio chloroform:Methanol:Ice Acetic acid=90:8:2）System anlysis surface only product is extracted in organic phase.
It is optimal by above-mentioned experiment surface PH=5 in acidization, the impurity for being extracted into organic phase is minimum, extraction The object got in organic phase is most pure.

Claims (5)

1. a kind of synthetic method of N α-fluorenylmethyloxycarbonyl-hydroxytyrosines, it is characterized in that comprising the following steps：
A, DL- m-Tyrosines are dissolved in aqueous slkali, add ice-water bath after acetone and be cooled to 0 DEG C, add fluorenes methoxy carbonyl acyl succinyl Imines, regulation solution pH value=8-9, TLC tracks to reaction end；
B, reaction solution add ethyl acetate through suction filtration, extraction, and acidified, layering, extraction, TLC detection products are extracted completely Anhydrous sodium sulfate drying is stayed overnight into ethyl acetate phase, then after the washing of overpickling, washing and saturated common salt；Filtering and washing nothing Then aqueous sodium persulfate, vacuum distillation solvent, plus petroleum ether stand to there is white opacity；
C, product will be stood it is dissolved in aqueous slkali, adds ether, acidified, layering, extraction, TLC detection products are extracted completely Into ether phase, ether phase is washed, saturated common salt washing ether phase, anhydrous sodium sulfate drying is stayed overnight；Filtering, washs anhydrous slufuric acid Sodium, vacuum distillation solvent, plus petroleum ether are to white opacity, you can separate out white solid product.
2. the synthetic method of a kind of N α-fluorenylmethyloxycarbonyl-hydroxytyrosines according to claim 1, it is characterized in that step Aqueous slkali described in rapid a is one or both of sodium carbonate, sodium acid carbonate, sodium hydroxide mixed solution.
3. the synthetic method of a kind of N α-fluorenylmethyloxycarbonyl-hydroxytyrosines according to claim 2, it is characterized in that step Aqueous slkali described in rapid a is the sodium carbonate of mass percentage concentration 10% and the sodium acid carbonate mixed solution of mass percentage concentration 5%.
4. the synthetic method of a kind of N α-fluorenylmethyloxycarbonyl-hydroxytyrosines according to claim 1, it is characterized in that step Acidifying described in rapid b, c uses solid citric acid for adjusting pH value=3-5.
5. the synthetic method of a kind of N α-fluorenylmethyloxycarbonyl-hydroxytyrosines according to claim 4, it is characterized in that pH Value=5.
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CN107722107A (en) * 2017-11-28 2018-02-23 陕西慧康生物科技有限责任公司 A kind of preparation method of acetyl group tetrapeptide 2
CN110015978A (en) * 2019-04-29 2019-07-16 康化（上海）新药研发有限公司 O- [2- [[tertbutyloxycarbonyl] amino] ethyl]-N- [fluorenylmethyloxycarbonyl]-l-tyrosine synthetic method
CN110078643A (en) * 2019-05-27 2019-08-02 吉尔生化（上海）有限公司 The synthetic method of hydroxytyrosine between a kind of N α-tertbutyloxycarbonyl-DL-
CN114560775A (en) * 2022-03-17 2022-05-31 绵阳师范学院 Preparation method of (R, S) -7-fluoro-1, 1, 3-trimethyl-2, 3-dihydro-1H-indene-4-amine

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107722107A (en) * 2017-11-28 2018-02-23 陕西慧康生物科技有限责任公司 A kind of preparation method of acetyl group tetrapeptide 2
CN110015978A (en) * 2019-04-29 2019-07-16 康化（上海）新药研发有限公司 O- [2- [[tertbutyloxycarbonyl] amino] ethyl]-N- [fluorenylmethyloxycarbonyl]-l-tyrosine synthetic method
CN110015978B (en) * 2019-04-29 2021-03-19 康化（上海）新药研发有限公司 Synthesis method of O- [2- [ [ (tert-butyloxycarbonyl) amino ] ethyl ] -N- [ fluorenylmethoxycarbonyl ] -L-tyrosine
CN110078643A (en) * 2019-05-27 2019-08-02 吉尔生化（上海）有限公司 The synthetic method of hydroxytyrosine between a kind of N α-tertbutyloxycarbonyl-DL-
CN114560775A (en) * 2022-03-17 2022-05-31 绵阳师范学院 Preparation method of (R, S) -7-fluoro-1, 1, 3-trimethyl-2, 3-dihydro-1H-indene-4-amine
CN114560775B (en) * 2022-03-17 2023-08-22 绵阳师范学院 Preparation method of (R, S) -7-fluoro-1, 3-trimethyl-2, 3-dihydro-1H-indene-4-amine

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Application publication date: 20170811