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:
-
- 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)
- Patent Classifications (CPCs):
-
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07F - ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- 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 = {Wed Jan 01 00:00:00 EST 1992},
month = {Wed Jan 01 00:00:00 EST 1992}
}