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Title: Enantioselective synthesis of L-(-)-4- boronophenylalanine (L-BPA)

Abstract

A method of making substantially pure L-BPA is disclosed. The method includes the steps of reacting 4-bromobenzaldehyde with ethylene glycol to form 4-bromobenzaldehyde ethylene glycol acetal, sequentially reacting 4-bromobenzaldehyde ethyleneglycol acetal with Mg to produce the Grignard reagent and thereafter reacting with tributyl borate and then converting to an acid environment to form 4-boronobenzaldehyde, reacting 4-boronobenzaldehyde with diethanol amine to form 4-boronobenzaldehyde diethanolamine ester, condensing the 4-boronobenzaldehyde diethanolamine ester with 2-phenyl-2-oxazolin-5-one to form an azlactone, reacting the azlactone with an alkali metal hydroxide to form z-[alpha]-benzoylamino-4boronocinnamic acid, asymmetrically hydrogenating the z-[alpha]-benzoylamino-4-boronocinnamic acid in the presence of a catalyst of a cheltate complex of rhodium (I) with chiral bisphosphines to form L-(+)-N-benzoyl-4-boronophenylalanine, and thereafter acidifying the L-(+)-N-benzoyl-4-boronophenylalanine in an organic medium to produce L-BPA. 3 figs.

Inventors:
Issue Date:
OSTI Identifier:
7233226
Patent Number(s):
5157149 A
Application Number:
PPN: US 7-710208
Assignee:
Dept. of Energy, Washington, DC (United States) PTO; EDB-94-089408
DOE Contract Number:  
AC07-76ID01570
Resource Type:
Patent
Resource Relation:
Patent File Date: 4 Jun 1991
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; BENZALDEHYDE; CHEMICAL REACTIONS; GLYCOLS; REAGENTS; SYNTHESIS; ALCOHOLS; ALDEHYDES; HYDROXY COMPOUNDS; ORGANIC COMPOUNDS; 400201* - Chemical & Physicochemical Properties

Citation Formats

Samsel, E.G. Enantioselective synthesis of L-(-)-4- boronophenylalanine (L-BPA). United States: N. p., 1992. Web.
Samsel, E.G. Enantioselective synthesis of L-(-)-4- boronophenylalanine (L-BPA). United States.
Samsel, E.G. Tue . "Enantioselective synthesis of L-(-)-4- boronophenylalanine (L-BPA)". United States.
@article{osti_7233226,
title = {Enantioselective synthesis of L-(-)-4- boronophenylalanine (L-BPA)},
author = {Samsel, E.G.},
abstractNote = {A method of making substantially pure L-BPA is disclosed. The method includes the steps of reacting 4-bromobenzaldehyde with ethylene glycol to form 4-bromobenzaldehyde ethylene glycol acetal, sequentially reacting 4-bromobenzaldehyde ethyleneglycol acetal with Mg to produce the Grignard reagent and thereafter reacting with tributyl borate and then converting to an acid environment to form 4-boronobenzaldehyde, reacting 4-boronobenzaldehyde with diethanol amine to form 4-boronobenzaldehyde diethanolamine ester, condensing the 4-boronobenzaldehyde diethanolamine ester with 2-phenyl-2-oxazolin-5-one to form an azlactone, reacting the azlactone with an alkali metal hydroxide to form z-[alpha]-benzoylamino-4boronocinnamic acid, asymmetrically hydrogenating the z-[alpha]-benzoylamino-4-boronocinnamic acid in the presence of a catalyst of a cheltate complex of rhodium (I) with chiral bisphosphines to form L-(+)-N-benzoyl-4-boronophenylalanine, and thereafter acidifying the L-(+)-N-benzoyl-4-boronophenylalanine in an organic medium to produce L-BPA. 3 figs.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {1992},
month = {10}
}