ChemicalBook CAS DataBase List L-Homophe-OH

L-Homophe-OH synthesis

9synthesis methods

Product Name:L-Homophe-OH
CAS Number:943-73-7
Molecular formula:C10H13NO2
Molecular Weight:179.22

Asymmetric reduction of prochiral ketone remains one of the most investigated methods to date for production of chiral L-homophenylalanine. One of the most established method for synthesizing L-homophenylalanine on a laboratory scale was carried out via enzyme-catalyzed asymmetric synthesis of keto acids. In this method, prochiral ketone was converted via reductive amination to enantiopure products with bulky side chains by addition of biocatalysts such as L-homophenylalanine dehydrogena. in the presence of cofactor. L-phenylalanine dehydrogenase is by and large preferred as it has mainly a catabolic function and accepts a wide variety of keto acids as substrates hence it is generally employed in the synthesis of L-homophenylalanine which carries very bulky side chains[1].

Benzenebutanoic acid, α-amino-, sodium salt (1:1), (αS)-

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Yield:943-73-7 89.6%

Reaction Conditions:

with hydrogenchloride;sodium hydroxide in water;

Steps:

14 EXAMPLE 14

EXAMPLE 14 10.0 g of homophenylalanine sodium salt are dissolved in 60 ml of deionised water and the solution is added dropwise over 1 hour to 24 ml of 2N hydrochloric acid to form a white, faintly lustrous crystalline suspension. This suspension is adjusted with 1N sodium hydroxide solution to pH 4.0 and then stirred for 2 hours at room temperature and filtered. The filter product is washed with deionised water and dried at room temperature in a high vacuum, affording pure (+)-S-homophenylalanine with an angle of rotation of [α]_D²⁰ =+45.6° (1%, 1N hydrochloric acid). Melting point: 287°-290° C. Yield: 89.6%.

References:

US4785089,1988,A