The Study of the Isomarization of α,α Diphenyl-Prolinol
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The approach to synthesize racemic α,α-diphenyl-prolinol was investigated. The first step was to cyclize glutamic acid to yield 5-oxoproline by refluxing with water overnight. In the first approach, the attempt was made to protect 5-oxoproline using benzylchloroformate as a protecting group. This method of attaching CBZ protecting group turned out to be unsuccessful. Therefore, the alternate approach was purposed. In this synthesis, the first step also started with cyclize glutamic acid to 5-oxoproline. However, instead of attaching the CBZ protecting group to 5-oxoproline, 5-oxoproline was converted to methylpyroglutamate first. Two protection groups were examined to determine which protecting group was better suited for this particular reaction. So far, the results suggest that using di-tert-butyl dicarbonate as a protecting group is preferable for this particular reaction than benzylchloroformate due to a higher yield and purity of product. The progress of obtaining the final product is ongoing at this time. Although the results are not confirmed, the understanding of the degradation of l-prolinol, a precursor of CBS reagent, can be used to suggest the most sufficient way to synthesize the CBS reagent, which could improve the synthesis of Phomactin B2.