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

Patent ·
OSTI ID:868509
 [1]
  1. Baton Rouge, LA
+ Show Author Affiliations

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.

Research Organization:
EG & G IDAHO INC
DOE Contract Number:
AC07-76ID01570
Assignee:
United States of America as represented by United States (Washington, DC)
Patent Number(s):
US 5157149
OSTI ID:
868509
Country of Publication:
United States
Language:
English

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Related Subjects

-4-
-benzoylamino-4-boronocinnamic
-n-benzoyl-4-boronophenylalanine
/999/260/
2-phenyl-2-oxazolin-5-one
4-boronobenzaldehyde
4-bromobenzaldehyde
acetal
acid
acidifying
alkali
alkali metal
alpha
amine
asymmetrically
azlactone
bisphosphines
borate
boronophenylalanine
catalyst
cheltate
chiral
complex
condensing
converting
diethanol
diethanolamine
disclosed
enantioselective
environment
ester
ethylene
ethylene glycol
ethyleneglycol
form
glycol
grignard
grignard reagent
hydrogenating
hydroxide
l-
l-bpa
medium
metal
metal hydroxide
method
mg
organic
organic medium
presence
produce
pure
reacting
reagent
rhodium
selective synthesis
sequentially
steps
substantially
substantially pure
synthesis
thereafter
tributyl
z-