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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-4-boronocinnamic 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.

Inventors:
 [1]
  1. (Baton Rouge, LA)
Issue Date:
Research Org.:
EG & G IDAHO INC
OSTI Identifier:
868509
Patent Number(s):
5157149
Assignee:
United States of America as represented by United States (Washington, DC) INEEL
DOE Contract Number:  
AC07-76ID01570
Resource Type:
Patent
Country of Publication:
United States
Language:
English
Subject:
enantioselective; synthesis; l-; -4-; boronophenylalanine; l-bpa; method; substantially; pure; disclosed; steps; reacting; 4-bromobenzaldehyde; ethylene; glycol; form; acetal; sequentially; ethyleneglycol; mg; produce; grignard; reagent; thereafter; tributyl; borate; converting; acid; environment; 4-boronobenzaldehyde; diethanol; amine; diethanolamine; ester; condensing; 2-phenyl-2-oxazolin-5-one; azlactone; alkali; metal; hydroxide; z-; alpha; -benzoylamino-4-boronocinnamic; asymmetrically; hydrogenating; presence; catalyst; cheltate; complex; rhodium; chiral; bisphosphines; -n-benzoyl-4-boronophenylalanine; acidifying; organic; medium; ethylene glycol; substantially pure; alkali metal; metal hydroxide; selective synthesis; grignard reagent; organic medium; /999/260/

Citation Formats

Samsel, Edward G. Enantioselective synthesis of L-(-)-4- boronophenylalanine (L-BPA). United States: N. p., 1992. Web.
Samsel, Edward G. Enantioselective synthesis of L-(-)-4- boronophenylalanine (L-BPA). United States.
Samsel, Edward G. Wed . "Enantioselective synthesis of L-(-)-4- boronophenylalanine (L-BPA)". United States. https://www.osti.gov/servlets/purl/868509.
@article{osti_868509,
title = {Enantioselective synthesis of L-(-)-4- boronophenylalanine (L-BPA)},
author = {Samsel, Edward 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-4-boronocinnamic 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.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {1992},
month = {1}
}

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