Scalable and Cost-Effective Synthetic Process for the Preparation of l-3,4-Dihydroxyphenylalanine─Levodopa,Organic Process Research & Development

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Scalable and Cost-Effective Synthetic Process for the Preparation of l-3,4-Dihydroxyphenylalanine─Levodopa
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2023-12-29 , DOI: 10.1021/acs.oprd.3c00313
Ramesh Goura _{1,

2} , Surendra Babu Manabolu Surya ₁ , Naresh Kumar Katari ₁ , Ramprasad Achampeta Kodanda ₂ , Pradeep Rebelly ₂ , Nagaraju Chakilam ₂

Affiliation

We reported the development of a novel synthetic process for Levodopa (1), which involves two simple chemical steps. The first step includes the reaction of l-tyrosine (18) with aqueous hydrogen bromide (HBr) to yield 3-bromo-l-tyrosine (19). The second step involves hydroxylation using an alkali base and copper iodide as a catalyst to produce Levodopa (1) with good quality and an overall yield of 41.75%. This new synthetic approach offers several advantages, including good reactivity, low cost, mitigation of the poor solubility issues associated with the reported process, and finally, it is industrially viable and capable of controlling the quality of the final Levodopa drug substance.

中文翻译：

用于制备l-3,4-二羟基苯丙氨酸─左旋多巴的可扩展且具有成本效益的合成工艺

我们报道了一种新的左旋多巴合成工艺 (1) 的开发，该工艺涉及两个简单的化学步骤。第一步包括使1-酪氨酸(18)与溴化氢(HBr)水溶液反应生成3-溴-1-酪氨酸(19)。第二步采用碱和碘化铜为催化剂进行羟基化，生产出质量良好的左旋多巴(1)，总收率41.75%。这种新的合成方法具有多种优点，包括良好的反应性、低成本、减轻与所报道的工艺相关的溶解度差问题，最后，它在工业上可行并且能够控制最终左旋多巴原料药的质量。

更新日期：2023-12-29

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