CN101353312B - 苯甘氨酸衍生物的合成 - Google Patents
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Abstract
本发明提供了一种苯甘氨酸衍生物的合成方法，将取代苯甘氨酸和乙酰乙酸酯在碳酸钾和醇溶剂存在下反应得到苯甘氨酸衍生物。本发明合成方法得到的产品中钾盐杂质含量低，产品的稳定性大大提高，易于运输和储存；同时生产原料易得，操作简便，生产过程中减少了工业废水的排放，减轻了环保压力。
Description
技术领域
本发明涉及医药化工领域中医药中间体的合成，特别涉及一种抗生素药物中间体的合成。
背景技术
苯甘氨酸衍生物为抗生素重要的中间体，是合成β-内酰胺类，半合成抗菌素的侧链。WO9101968A1公开了一种采用对羟基苯甘氨酸和乙酰乙酸乙酯在氢氧化钾存在下反应得到目标产物对羟基苯甘氨酸邓钾盐的方法。该合成方法中采用的原料氢氧化钾中含有较多的氯化钾杂质，导致投料量难以确定，氯化钾带入最终产品中难以除去。产品的纯度和收率较低，产品的稳定性差，生产成本高，不适合工业化生产。
发明内容
本发明提供一种收率高、环保压力小、适合工业化生产的苯甘氨酸衍生物的合成方法，得到的产品纯度高，易于运输和储存。
一种苯甘氨酸衍生物的合成方法，包括：取代苯甘氨酸和乙酰乙酸酯在碳酸钾和醇溶剂的存在下进行反应，经后处理得到具有结构通式(III)的苯甘氨酸衍生物；
其中R1为氢、羟基、甲氧基、乙氧基、苄氧基、苄氧羰基、甲基、氟、氯、溴或硝基；R2为C1-C5的直链或支链烷基。
所述的取代苯甘氨酸具有结构通式(I)；
所述的乙酰乙酸酯具有结构通式(II)；
结构通式(I)和结构通式(II)中的R1、R2与结构通式(III)中具有相同含义。
本发明合成方法反应式如下：
所述的R2为甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基、异丁基、正戊基。
所述的醇溶剂为C1-C5的醇类，具体选自甲醇、乙醇、正丙醇、异丙醇、正丁醇、仲丁醇、叔丁醇或正戊醇。
所述的合成方法中各物料的摩尔比为，取代苯甘氨酸：溶剂：碳酸钾：乙酰乙酸酯＝1：10～50：0.5～0.75：1～1.2。
本发明合成方法具体操作如下：将取代苯甘氨酸、溶剂、碳酸钾和乙酰乙酸酯混合，搅拌均匀，升温至40～60℃，反应0.5～4小时，直至反应完全，进行后处理时先降温至35℃以下，再抽滤，干燥，得到苯甘氨酸衍生物湿品，得到的湿品在40～70℃减压烘干即可。
经研究表明现有技术反应过程中生成了副产物水，溶解了一部分产品，使得产品收率降低；本发明采用碳酸钾为原料，避免了大量水的生成，同时提高了无机钾盐在体系中的融合性，减少了碱的用量，降低了生产成本。
现有技术的产品中有微量的氢氧化钾在产品中难以除去，从而影响产品的储存，本发明采用碳酸钾避免了采用碱性很强的氢氧化钾，延长了产品的储存期限。
本发明选用碳酸钾作为原料合成苯甘氨酸衍生物，产品中钾盐杂质含量低，产品的稳定性大大提高，易于运输和储存；同时生产原料易得，操作简便，生产过程中减少了工业废水的排放，减轻了环保压力。
具体实施方式
实施例1
按照各物料摩尔比为对羟基苯甘氨酸：乙醇：碳酸钾：乙酰乙酸甲酯＝1：30：0.60：1进行如下反应：
取0.5mol对羟基苯甘氨酸、乙醇、碳酸钾、乙酰乙酸甲酯投入2000ml三口瓶中，加毕后升温至55℃，反应2小时，反应结束，降温至25℃，抽滤得湿品，湿品在50℃减压烘干，得到目标产物，含量≥99.5％，收率95％。
实施例2
按照各物料摩尔比为对氯苯甘氨酸：正丙醇：碳酸钾：乙酰乙酸乙酯＝1：20：0.5：1.05进行如下反应：
取0.4mol对氯苯甘氨酸、正丙醇、碳酸钾、乙酰乙酸乙酯投入2000ml三口瓶中，加毕后升温至40℃，反应4小时，反应结束，降温至25℃，抽滤得湿品，湿品在40℃减压烘干，得到目标产物，含量≥99.5％，收率94.8％。
实施例3
按照各物料摩尔比为对甲基苯甘氨酸：正丁醇：碳酸钾：乙酰乙酸丙酯＝1：40：0.75：1.2进行如下反应：
取1mol对甲基苯甘氨酸、正丁醇、碳酸钾、乙酰乙酸丙酯酯投入2000ml三口瓶中，加毕后升温至50℃，反应3小时，反应结束，降温至25℃，抽滤得湿品，湿品在60℃减压烘干，得到目标产物，含量≥99.5％，收率95.6％。
实施例4
按照各物料摩尔比为对甲氧基苯甘氨酸：叔丁醇：碳酸钾：乙酰乙酸叔丁酯＝1：50：0.70：1.2进行如下反应：
取0.5mol对甲氧基苯甘氨酸、叔丁醇、碳酸钾、乙酰乙酸叔丁酯投入2000ml三口瓶中，加毕后升温至60℃，反应1小时，反应结束，降温至25℃，抽滤得湿品，湿品在70℃减压烘干，得到目标产物，含量≥99.5％，收率95％。
实施例5
按照各物料摩尔比为苯甘氨酸：异丙醇：碳酸钾：乙酰乙酸戊酯＝1：15：0.65：1.15进行如下反应：
取0.5mol苯甘氨酸、异丙醇、碳酸钾、乙酰乙酸乙酯投入2000ml三口瓶中，加毕后升温至50℃，反应4小时，反应结束，降温至25℃，抽滤得湿品，湿品在50℃减压烘干，得到目标产物，含量≥99.5％，收率94.8％。
实施例6
按照各物料摩尔比为对苄氧基苯甘氨酸：甲醇：碳酸钾：乙酰乙酸甲酯＝1：45：0.60：1.1进行如下反应：
取1mol对苄氧基苯甘氨酸、甲醇、碳酸钾、乙酰乙酸甲酯酯投入2000ml三口瓶中，加毕后升温至60℃，反应2小时，反应结束，降温至25℃，抽滤得湿品，湿品在60℃减压烘干，得到目标产物，含量≥99.5％，收率95.6％。
Claims (3)
1.一种苯甘氨酸衍生物的合成方法，包括：取代苯甘氨酸和乙酰乙酸酯在碳酸钾和有机溶剂的存在下进行反应，反应的温度为40～60℃，反应的时间为0.5～4小时，反应原料的摩尔比为取代苯甘氨酸∶溶剂∶碳酸钾∶乙酰乙酸酯＝1∶10～50∶0.5～0.75∶1～1.2；所述的有机溶剂为C1-C5的醇类；经后处理得到具有结构通式(Ⅲ)的苯甘氨酸衍生物；
其中R1为氢、羟基、甲氧基、乙氧基、苄氧基、苄氧羰基、萘基、甲基、氟、氯、溴或硝基；R2为C1-C5的直链或支链烷基；
所述的取代苯甘氨酸具有结构通式(I)；
所述的乙酰乙酸酯具有结构通式(II)；
结构通式(I)和结构通式(II)中的R1、R2与结构通式(III)中具有相同含义。
2.如权利要求1所述的合成方法，其特征在于：所述的R2为甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、正戊基。
3.如权利要求1所述的合成方法，其特征在于：所述的醇为甲醇、乙醇、正丙醇、异丙醇、正丁醇、仲丁醇、叔丁醇或正戊醇。
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