Q50. What steps are needed to convert... [FREE SOLUTION]

Chapter 29: Q50. (page 1194)

What steps are needed to convert A to L-dopa, an uncommon amino acid that is effective in treating Parkinson鈥檚 disease? These steps are the key reactions in the first commercial asymmetric synthesis using a chiral transition metal catalyst. This process was developed at Monsanto in 1974.

Short Answer

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The steps needed to convert A to L-dopa are shown below:

Step by step solution

L-dopa

L-dopa is an organic compound containing amino groups and is used to treat symptoms linked with Parkinson鈥檚 disease.It can be synthesized from L-Tyrosine, and dopamine is synthesized from L-dopa.

Steps needed to convert A to L-dopa

When A is treated with $H_{2}$ in the presence of a chiral Rh catalyst, an alkene is reduced to alkane. Further, on treatment with a strong acid, ${NHCOCH}_{2}$ (amide group) is converted to ${NH}_{2}$ (amine group), the methoxy group is converted to OH, and the ${CH}_{3} COO$ group is converted to OH. This leads to the formation of L-dopa. The steps required to convert A to L-dopa are shown below: