以L-苯丙氨酸为“手性源”合成（S）-吲哚啉-2-甲酸及其衍生物
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摘要
(S)-吲哚啉-2-甲酸及其衍生物是天然产物中广泛存在的结构片段,也是众多对心血管疾病有治疗保健作用的药物的特征结构片段,其合成难度大,传统方法存在路线长、收率低、成本高等问题,是影响相关药物制造成本的关键因素。
(S)-吲哚啉-2-甲酸与L-苯丙氨酸的化学结构相似,手性中心相同,因此,本文提出了一种以L-苯丙氨酸为“手性源”,经引入辅助基团、分子内胺化成环、定向合成(S)-吲哚啉-2-甲酸的方法。L-苯丙氨酸为天然氨基酸,来源广泛,价格低廉,该方法具有反应步骤少、无需使用拆分剂、成本低、污染少、可从原料手性确定产物构型等优点。
为保证L-苯丙氨酸的邻位取代顺利进行,需在其对位引入间位定位基团,本文选择硝基为辅助基团,定位效应强,生产成本低。
首先,研究了混酸法合成4-硝基-L-苯丙氨酸的工艺。结果发现,釜式混酸硝化时反应时间长,生成的2-硝基-L-苯丙氨酸和4-硝基-L-苯丙氨酸易与浓硫酸发生缩合反应,是釜式反应收率较低的主要原因,为缩短停留时间、减少返混,特设计了管式反应器,抑制副反应,产物收率提高明显,并以正交实验优化了反应条件,在混酸中硝酸与硫酸体积比为2：1,50℃停留5min,产品收率可达80.9%。
文献报道的混酸法难以直接制备2,4-二硝基-L-苯丙氨酸,其主要原因是第二个硝基的引入需要相对较高的反应温度,此时,混酸具有强氧化性,易将L-苯丙氨酸侧链上的苄基很氧化,得到苯甲酸衍生物。
研究了以硝酸脲为硝化剂,以4-硝基-L-苯丙氨酸为原料,在硫酸中制备2,4-二硝基-L-苯丙氨酸的工艺,优化的工艺条件为：在60℃下反应6h,硝化剂与原料摩尔比为1.2：1,产品收率达87.7%。讨论了硝化机理,认为尿素的存在降低了硝酸的氧化性,提高了硝酰正离子的亲电能力,能够实现二硝化反应。
尝试了以硝酸脲为硝化剂对L-苯丙氨酸的“一锅法”硝化制备2,4-二硝基-L-苯丙氨酸的工艺。分析了反应能够进行的原因,认为反应中硫酸浓度非常重要。优化了工艺条件,反应分段进行：前期单硝化时,硝酸脲与底物摩尔比为1：1,冰水浴反应2 h；后期二硝化时,补加1.2倍量的硝酸脲,在60℃反应4 h,2,4-二硝基-L-苯丙氨酸收率可达75.7%。
为获得高纯度的2,4-二硝基-L-苯丙氨酸,测定了其在十种溶剂中的溶解度,结果表明正丙醇是合适的重结晶溶剂,以该溶剂对2,4-二硝基苯丙氨酸重结晶,可以得到高于99.5%纯度的产品,重结晶母液仍可循环使用。并用Apelblat方程对溶解度数据进行了回归,发现均方差不超过2.5%。
着重研究了影响关键步骤2,4-二硝基-L-苯丙氨酸的分子内环合反应的因素,发现反应随温度和压力变化收率变化很大,以水为溶剂,在180℃下反应6 h,可以44.5%的收率得到6-硝基-(S)-吲哚啉-2-甲酸,其e.e.值高于99%。采用密度泛函理论对分子内氨基取代硝基的反应进行了量子化学计算,结果表明,分子内环合反应脱除亚硝酸生成6-硝基-(S)-吲哚啉-2-甲酸的反应在热力学上优于分子内脱水副反应,脱除亚硝酸释放的能量更多,产物更稳定。氨基取代硝基的反应可用于制备有机胺的反应,扩展了胺取代硝基的反应,选用了不同的硝基底物与胺,发现在相似的条件下,均三硝基苯和二硝基苯均能以较好的收率得到硝基苯胺衍生物,分析了反应机理,认为可能是由于一个硝基使另一个的活性上升所致,而硝基苯和胺分别为硬酸和硬碱,易于反应,是该反应能够进行的主要原因。
为了获得更好的6-硝基-(S)-吲哚啉-2-甲酸的总收率,讨论了4-硝基-L-苯丙氨酸溴化环合的工艺,优化了该反应的工艺条件。其中,溴化反应以三溴异氰脲酸酯为溴化试剂,在室温反应3 h可以72.6%的收率得到2-溴-4-硝基-L-苯丙氨酸,其分子内Ullmann反应在氯化亚铜催化下进行,以碳酸钾为碱、水为溶剂,在回流温度下反应4 h,收率可达90.5%,产物没有发生消旋现象。详细讨论了各种溴化试剂的反应机理,认为三溴异氰脲酸在浓硫酸中能够多质子化,是其有效将溴正离子转移至钝化芳环的主要原因。
6-硝基-(S)-吲哚啉-2-甲酸经催化还原、重氮化、去重氮基的“一锅”反应制备得到了(S)-吲哚啉-2-甲酸。三步反应在“一锅”内进行,反应过程的较优工艺条件为：还原反应中,使用5%钯碳为催化剂催化加氢,以水为溶剂,氢气压力为0.5 MPa,60℃反应4 h；重氮化反应在冰水浴中反应3 h；脱除重氮基的反应在55℃下反应3 h。在上述条件下,三步反应的总收率可达85.9%,e.e.值高于99.5%。
(S)-吲哚啉-2-甲酸在Pd/C催化下,可还原为(2S,3aS,7aS)-八氢吲哚-2-甲酸,将其固载在Wang树脂载体上,与预先合成的N-[1-(S)-乙氧羰基丁基]-(S)-丙氨酸反应,可制备培哚普利,收率可达87.8%,将培哚普利与叔丁胺反应,制备得到了临床上广泛使用的培哚普利叔丁胺盐。
反应过程的相关中间体和产物结构均经过了IR,1HNMR和13CNMR等检测,证明结果正确,所有中间体和产物的旋光度均经过检测,其e.e.值均经过手性柱进行HPLC分析,结果表明其e.e.均高于99%。
(S)-Indoline-2-carboxylic acid and its derivatives are common building block in natural products and it is the characteristic structure fragment of many drugs which are effective for cardiovascular diseases treatment. The synthesis of (S)-indoline-2-carboxylic acid suffers from much difficulty. Multistep, low yield and high cost, which are the main drawback in traditional methods, contribute the ex-tremely high cost of related drugs. The great similarities both in chemical structure and stereochemical configuration between (S)-indo line-2-carboxy lic acid and L-phenylalanine inspire us to carry out a chiral pool route from L-phenylalanine for its facile commercial availability and low price. Thus, this dissertation presents a chiral pool route for the synthesis of (S)-indoline-2-carboxylic acid following the procedure combined with assistant-group introduction and intramolecular ami-no-cycling. It benefits from wide raw material source, concise route, no resolution reagent, low cost, less pollution release and specific configuration.
A blocking group is needed in the para position of L-phenylalanine for its subs-titution will firstly occur at that position. A meta guiding group will ensure the second substitution taking place at the ortho place of L-phenylalanine. In this dissertation, nitro group was adopted for its powerful guiding capability and low cost.
The nitration of L-phenylalanine with mixed acid could give 4-nitro-L-phenylalanine in low yield with traditional batch reaction. The structure of the by-product was confirmed with 1H-NMR and 13C-NMR. And it is thought to be the con-densation of 2-nitro-L-phenylalanine and 4-nitro-L-phenylanine with sulfuric acid. Based on this, the possible mechanism was proposed and a new tubular reactor was designed. With the tubular reactor,4-nitro-L-phenylalanine can be got in 80.9% yield with optimized conditions as 50℃for 5min in vHNO3:vH2SO4=1:2. The synthesis of 2,4-dinitro-L-phenylalanine following previous way was a failure. The results showed that the main product was 2,4-dinitro benzoic acid instead of 2,4-dinitro-L-phenylalanine. And the reason is that the mixed acid showed high oxid- ative capability and the amino acid moisture was cleaved from the benyl site. Subs-quently, the preparation of 2,4-dinitro-L-phenylalanine follows a stepwise procedure.
The nitration of 4-nitro-L-phenylalanine with urea nitrate/H2SO4 affords 2,4-dintro-L-phenylalanine in 87.8% yield at 60℃for 6h. The possible mechanism was discussed. It was thought that the urea greatly decreased the oxidative capability of nitric acid and enhanced the electrophilicity of NO2
As sulfuric acid was the only solvent in both nitation, "one-pot" way was tried to synthesize 2,4-dinitro-L-phenylalanine. And the results demonstrated that it could not get the product with nitric acid and urea nitrate as the nitrating reagents for the huge water contained in nitric acid but could give the product with urea nitrate as the sole nitrating reagent. The optimized "one-pot" procedure was 75.7% yield-reaction oper-ated as follows:ice-water bath for 2h with lmole ratio urea nitrate, after that an addi-tional 1.2 mole of urea nitrate was added, the temperature was raised to 60℃, and kept for 4h.
The solubilities of 2,4-dinitro-L-phenylalanine in ten different solvents were measured with a synthetic method to find a proper recrystillization solvent to deal with its difficult workup process. And the solubility data was regressed with Apelblat founction. The results demonstrated that 1-propanol was a suitable solvent for its re-crystillization and Apelblat founction fitted the solubility data with a root-mean-square relative deviation (rmsrd) less than 2.5%.
The factors affecting intramolecular cyclization of 2,4-dinitro-L-phenylalanine was especially emphasized. Yields varied with the reaction temperature and pressure and 6-nitro-(S)-indoline-2-carboxylic acid could be got in 44.5% yield at 180℃for 6h in water with e.e. higher than 99%. Density founctional theory (DFT) was used to investigate the reaction. Results showed that the intramolecular reaction was the do-minating reaction and the reason why the reaction could proceed was that the intra-molecular cylization released more energy than the side reaction. The nitro amination reaction was researched in detail with expanded substrates and amines. Similar or higer yield could be got under similar conditions with trinitrobenzene and dinitroben-zenes as substrates. The possible mechanism was that the remaining nitro group could enhance the activity of the leaving one and that the nitrobenzene analogues and amines were hard acid and hard base, respectively, which properly matched.
Meanwhile, another process was successfully performed starting with 4-nitro-L-phenylalnine through bromination and cyclization for the low yields of its nitro amination. The bromination with tribromoisocyanuric acid (TBCA) in H2SO4 at room temperature could give 72.6% yield of 2-bromo-4-nitro-L-phenylalanine, of which the intramolecular Ullmann reaction catalyzed by CuCl can give 6-nitro-(S)-indoline-2-carboxylic acid in 90.5% yield with water as solvent and K2CO3 as base. No racemizition was observed in the whole process and the enanti-omeric excess (e.e.) of product was higher than 99.5%. The possible mechanism was detailed discussed. Protonated tribromoisocyanuric acid (TBCA) can transfer Br to deactivated aromatics.
The subsequently nitro-reduction, diazo-reaction and dediazo-reaction of 6-nitro-(S)-indoline-2-carboxylic acid was carried out with a "one-pot" way to get (S)-indoline-2-carboxylic acid. The yield of the "one-pot" reaction was 85.9% under the optimized conditions.
(25,3aS,7aS)-Octahydroindole-2-carboxylic acid could be got with the reduc-tion of (S)-indo line-2-carboxylic acid catalyzed by 5% Pd/C with 75% yield, and it was loaded on Wang resin and subsequently react with N-[1-(S)-ethoxycarbonyl butyl]-(S)-glycine to prepare perindopril in 87.8% yield.
All the intermediates and product were confirmed with IR, 1HNMR and 13CNMR. The optical rotations were checked and the enantiomer excess (e.e.) were confirmed with chiral high performance liquid chromatography (HPLC), which showed more than 99% purity.
(S)-吲哚啉-2-甲酸与L-苯丙氨酸的化学结构相似,手性中心相同,因此,本文提出了一种以L-苯丙氨酸为“手性源”,经引入辅助基团、分子内胺化成环、定向合成(S)-吲哚啉-2-甲酸的方法。L-苯丙氨酸为天然氨基酸,来源广泛,价格低廉,该方法具有反应步骤少、无需使用拆分剂、成本低、污染少、可从原料手性确定产物构型等优点。
为保证L-苯丙氨酸的邻位取代顺利进行,需在其对位引入间位定位基团,本文选择硝基为辅助基团,定位效应强,生产成本低。
首先,研究了混酸法合成4-硝基-L-苯丙氨酸的工艺。结果发现,釜式混酸硝化时反应时间长,生成的2-硝基-L-苯丙氨酸和4-硝基-L-苯丙氨酸易与浓硫酸发生缩合反应,是釜式反应收率较低的主要原因,为缩短停留时间、减少返混,特设计了管式反应器,抑制副反应,产物收率提高明显,并以正交实验优化了反应条件,在混酸中硝酸与硫酸体积比为2：1,50℃停留5min,产品收率可达80.9%。
文献报道的混酸法难以直接制备2,4-二硝基-L-苯丙氨酸,其主要原因是第二个硝基的引入需要相对较高的反应温度,此时,混酸具有强氧化性,易将L-苯丙氨酸侧链上的苄基很氧化,得到苯甲酸衍生物。
研究了以硝酸脲为硝化剂,以4-硝基-L-苯丙氨酸为原料,在硫酸中制备2,4-二硝基-L-苯丙氨酸的工艺,优化的工艺条件为：在60℃下反应6h,硝化剂与原料摩尔比为1.2：1,产品收率达87.7%。讨论了硝化机理,认为尿素的存在降低了硝酸的氧化性,提高了硝酰正离子的亲电能力,能够实现二硝化反应。
尝试了以硝酸脲为硝化剂对L-苯丙氨酸的“一锅法”硝化制备2,4-二硝基-L-苯丙氨酸的工艺。分析了反应能够进行的原因,认为反应中硫酸浓度非常重要。优化了工艺条件,反应分段进行：前期单硝化时,硝酸脲与底物摩尔比为1：1,冰水浴反应2 h；后期二硝化时,补加1.2倍量的硝酸脲,在60℃反应4 h,2,4-二硝基-L-苯丙氨酸收率可达75.7%。
为获得高纯度的2,4-二硝基-L-苯丙氨酸,测定了其在十种溶剂中的溶解度,结果表明正丙醇是合适的重结晶溶剂,以该溶剂对2,4-二硝基苯丙氨酸重结晶,可以得到高于99.5%纯度的产品,重结晶母液仍可循环使用。并用Apelblat方程对溶解度数据进行了回归,发现均方差不超过2.5%。
着重研究了影响关键步骤2,4-二硝基-L-苯丙氨酸的分子内环合反应的因素,发现反应随温度和压力变化收率变化很大,以水为溶剂,在180℃下反应6 h,可以44.5%的收率得到6-硝基-(S)-吲哚啉-2-甲酸,其e.e.值高于99%。采用密度泛函理论对分子内氨基取代硝基的反应进行了量子化学计算,结果表明,分子内环合反应脱除亚硝酸生成6-硝基-(S)-吲哚啉-2-甲酸的反应在热力学上优于分子内脱水副反应,脱除亚硝酸释放的能量更多,产物更稳定。氨基取代硝基的反应可用于制备有机胺的反应,扩展了胺取代硝基的反应,选用了不同的硝基底物与胺,发现在相似的条件下,均三硝基苯和二硝基苯均能以较好的收率得到硝基苯胺衍生物,分析了反应机理,认为可能是由于一个硝基使另一个的活性上升所致,而硝基苯和胺分别为硬酸和硬碱,易于反应,是该反应能够进行的主要原因。
为了获得更好的6-硝基-(S)-吲哚啉-2-甲酸的总收率,讨论了4-硝基-L-苯丙氨酸溴化环合的工艺,优化了该反应的工艺条件。其中,溴化反应以三溴异氰脲酸酯为溴化试剂,在室温反应3 h可以72.6%的收率得到2-溴-4-硝基-L-苯丙氨酸,其分子内Ullmann反应在氯化亚铜催化下进行,以碳酸钾为碱、水为溶剂,在回流温度下反应4 h,收率可达90.5%,产物没有发生消旋现象。详细讨论了各种溴化试剂的反应机理,认为三溴异氰脲酸在浓硫酸中能够多质子化,是其有效将溴正离子转移至钝化芳环的主要原因。
6-硝基-(S)-吲哚啉-2-甲酸经催化还原、重氮化、去重氮基的“一锅”反应制备得到了(S)-吲哚啉-2-甲酸。三步反应在“一锅”内进行,反应过程的较优工艺条件为：还原反应中,使用5%钯碳为催化剂催化加氢,以水为溶剂,氢气压力为0.5 MPa,60℃反应4 h；重氮化反应在冰水浴中反应3 h；脱除重氮基的反应在55℃下反应3 h。在上述条件下,三步反应的总收率可达85.9%,e.e.值高于99.5%。
(S)-吲哚啉-2-甲酸在Pd/C催化下,可还原为(2S,3aS,7aS)-八氢吲哚-2-甲酸,将其固载在Wang树脂载体上,与预先合成的N-[1-(S)-乙氧羰基丁基]-(S)-丙氨酸反应,可制备培哚普利,收率可达87.8%,将培哚普利与叔丁胺反应,制备得到了临床上广泛使用的培哚普利叔丁胺盐。
反应过程的相关中间体和产物结构均经过了IR,1HNMR和13CNMR等检测,证明结果正确,所有中间体和产物的旋光度均经过检测,其e.e.值均经过手性柱进行HPLC分析,结果表明其e.e.均高于99%。
(S)-Indoline-2-carboxylic acid and its derivatives are common building block in natural products and it is the characteristic structure fragment of many drugs which are effective for cardiovascular diseases treatment. The synthesis of (S)-indoline-2-carboxylic acid suffers from much difficulty. Multistep, low yield and high cost, which are the main drawback in traditional methods, contribute the ex-tremely high cost of related drugs. The great similarities both in chemical structure and stereochemical configuration between (S)-indo line-2-carboxy lic acid and L-phenylalanine inspire us to carry out a chiral pool route from L-phenylalanine for its facile commercial availability and low price. Thus, this dissertation presents a chiral pool route for the synthesis of (S)-indoline-2-carboxylic acid following the procedure combined with assistant-group introduction and intramolecular ami-no-cycling. It benefits from wide raw material source, concise route, no resolution reagent, low cost, less pollution release and specific configuration.
A blocking group is needed in the para position of L-phenylalanine for its subs-titution will firstly occur at that position. A meta guiding group will ensure the second substitution taking place at the ortho place of L-phenylalanine. In this dissertation, nitro group was adopted for its powerful guiding capability and low cost.
The nitration of L-phenylalanine with mixed acid could give 4-nitro-L-phenylalanine in low yield with traditional batch reaction. The structure of the by-product was confirmed with 1H-NMR and 13C-NMR. And it is thought to be the con-densation of 2-nitro-L-phenylalanine and 4-nitro-L-phenylanine with sulfuric acid. Based on this, the possible mechanism was proposed and a new tubular reactor was designed. With the tubular reactor,4-nitro-L-phenylalanine can be got in 80.9% yield with optimized conditions as 50℃for 5min in vHNO3:vH2SO4=1:2. The synthesis of 2,4-dinitro-L-phenylalanine following previous way was a failure. The results showed that the main product was 2,4-dinitro benzoic acid instead of 2,4-dinitro-L-phenylalanine. And the reason is that the mixed acid showed high oxid- ative capability and the amino acid moisture was cleaved from the benyl site. Subs-quently, the preparation of 2,4-dinitro-L-phenylalanine follows a stepwise procedure.
The nitration of 4-nitro-L-phenylalanine with urea nitrate/H2SO4 affords 2,4-dintro-L-phenylalanine in 87.8% yield at 60℃for 6h. The possible mechanism was discussed. It was thought that the urea greatly decreased the oxidative capability of nitric acid and enhanced the electrophilicity of NO2
As sulfuric acid was the only solvent in both nitation, "one-pot" way was tried to synthesize 2,4-dinitro-L-phenylalanine. And the results demonstrated that it could not get the product with nitric acid and urea nitrate as the nitrating reagents for the huge water contained in nitric acid but could give the product with urea nitrate as the sole nitrating reagent. The optimized "one-pot" procedure was 75.7% yield-reaction oper-ated as follows:ice-water bath for 2h with lmole ratio urea nitrate, after that an addi-tional 1.2 mole of urea nitrate was added, the temperature was raised to 60℃, and kept for 4h.
The solubilities of 2,4-dinitro-L-phenylalanine in ten different solvents were measured with a synthetic method to find a proper recrystillization solvent to deal with its difficult workup process. And the solubility data was regressed with Apelblat founction. The results demonstrated that 1-propanol was a suitable solvent for its re-crystillization and Apelblat founction fitted the solubility data with a root-mean-square relative deviation (rmsrd) less than 2.5%.
The factors affecting intramolecular cyclization of 2,4-dinitro-L-phenylalanine was especially emphasized. Yields varied with the reaction temperature and pressure and 6-nitro-(S)-indoline-2-carboxylic acid could be got in 44.5% yield at 180℃for 6h in water with e.e. higher than 99%. Density founctional theory (DFT) was used to investigate the reaction. Results showed that the intramolecular reaction was the do-minating reaction and the reason why the reaction could proceed was that the intra-molecular cylization released more energy than the side reaction. The nitro amination reaction was researched in detail with expanded substrates and amines. Similar or higer yield could be got under similar conditions with trinitrobenzene and dinitroben-zenes as substrates. The possible mechanism was that the remaining nitro group could enhance the activity of the leaving one and that the nitrobenzene analogues and amines were hard acid and hard base, respectively, which properly matched.
Meanwhile, another process was successfully performed starting with 4-nitro-L-phenylalnine through bromination and cyclization for the low yields of its nitro amination. The bromination with tribromoisocyanuric acid (TBCA) in H2SO4 at room temperature could give 72.6% yield of 2-bromo-4-nitro-L-phenylalanine, of which the intramolecular Ullmann reaction catalyzed by CuCl can give 6-nitro-(S)-indoline-2-carboxylic acid in 90.5% yield with water as solvent and K2CO3 as base. No racemizition was observed in the whole process and the enanti-omeric excess (e.e.) of product was higher than 99.5%. The possible mechanism was detailed discussed. Protonated tribromoisocyanuric acid (TBCA) can transfer Br to deactivated aromatics.
The subsequently nitro-reduction, diazo-reaction and dediazo-reaction of 6-nitro-(S)-indoline-2-carboxylic acid was carried out with a "one-pot" way to get (S)-indoline-2-carboxylic acid. The yield of the "one-pot" reaction was 85.9% under the optimized conditions.
(25,3aS,7aS)-Octahydroindole-2-carboxylic acid could be got with the reduc-tion of (S)-indo line-2-carboxylic acid catalyzed by 5% Pd/C with 75% yield, and it was loaded on Wang resin and subsequently react with N-[1-(S)-ethoxycarbonyl butyl]-(S)-glycine to prepare perindopril in 87.8% yield.
All the intermediates and product were confirmed with IR, 1HNMR and 13CNMR. The optical rotations were checked and the enantiomer excess (e.e.) were confirmed with chiral high performance liquid chromatography (HPLC), which showed more than 99% purity.
引文
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