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

Details Enantioselective synthesis of L-(-)-4- boronophenylalanine (L-BP Enantioselective synthesis of L-(-)-4- boronophenylalanine (L-BP

1991-06-04

1992-10-20

Dees, Jose G.

Organic compounds -- part of the class 532-570 series

Organic compounds

Boron acids or salts thereof

260665G, 540467, 549455, 568 6, C07F 502

Patent

active

051571498

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.

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Snyder et al., Chemical Abstracts, vol. 52, No. 10923a (1958).

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