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
- Application Number:
- PPN: US 7-710208
- Assignee:
- Dept. of Energy, Washington, DC (United States)
- 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}
}