PL405495A1 - 2-amino-2-(4-dihydroxy boryl benzyl)-3-methylbutanoic acid metyl ester and method to produce it - Google Patents

2-amino-2-(4-dihydroxy boryl benzyl)-3-methylbutanoic acid metyl ester and method to produce it

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Publication number
PL405495A1
PL405495A1 PL40549513A PL40549513A PL405495A1 PL 405495 A1 PL405495 A1 PL 405495A1 PL 40549513 A PL40549513 A PL 40549513A PL 40549513 A PL40549513 A PL 40549513A PL 405495 A1 PL405495 A1 PL 405495A1
Authority
PL
Poland
Prior art keywords
amino
reaction
methyl ester
dihydroxyborylbenzyl
phenyl
Prior art date
Application number
PL40549513A
Other languages
Polish (pl)
Inventor
Tomasz Siódmiak
Marta Ziegler-Borowska
Michał Piotr Marszałł
Original Assignee
Uniwersytet Mikołaja Kopernika W Toruniu
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Uniwersytet Mikołaja Kopernika W Toruniu filed Critical Uniwersytet Mikołaja Kopernika W Toruniu
Priority to PL40549513A priority Critical patent/PL405495A1/en
Publication of PL405495A1 publication Critical patent/PL405495A1/en

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Abstract

Przedmiotem wynalazku są: nowy boronowy aminokwas posiadający fragment struktury 4-dihydroksyborylo-fenyloalaniny (BPA) i ?-podstawiony atom węgla fragmentem izopropylowym z zabezpieczoną grupą karboksylową: ester metylowy kwasu 2-amino-2- (4-dihydroksyborylobenzylo)-3-metylobutanowego o wzorze 1 i sposób jego wytwarzania. Sposób polega na tym, że ester metylowy kwasu 2-amino-2-(4-dihydroksyborylobenzylo) -3-metylobutanowego otrzymuje się z 4-bromotoluenu w wyniku reakcji metalacji-transmetalacji. Otrzymany 4-dihydroksyborylotoluen w reakcji z diolem przekształca się w 2-(4-metylo-fenylo)-[1,3,2]dioksaborolan, który poddaje się reakcji wolnorodnikowego bromowania otrzymując 2-(4-bromometylo-fenylo) -[1,3,2] dioksaborolan. Ester metylowy kwasu 2-(4-chlorobenzylidenoamino) -3-metylo-butanowego otrzymany z D,L-waliny w wyniku reakcji z chlorkiem tionylu i metanolem poddaje się reakcji z aldehydem 4-chlorobenzoesowym otrzymując iminę, którą przekształca się przez deprotonowanie w anion iminy, a następnie poddaje się reakcji z 2-(4-bromometylo-fenylo)-[1,3,2] dioksaborolanem. W ostatnim etapie działa się kwasem nieorganicznym uzyskując docelowy ester metylowy kwasu 2-amino-2-(4-dihydroksyborylobenzylo)-3-metylo-butanowego.The subject of the invention is: a new boronic amino acid having a fragment of 4-dihydroxyboryl-phenylalanine (BPA) structure and a α-substituted carbon atom with a carboxyl protected isopropyl fragment: 2-amino-2- (4-dihydroxyborylbenzyl) -3-methylbutanoic acid methyl ester Formula 1 and its method of preparation. The method consists in the fact that 2-amino-2- (4-dihydroxyborylbenzyl) -3-methylbutanoic acid methyl ester is obtained from 4-bromotoluene by metallation-transmetallation reaction. The 4-dihydroxyboryltoluene obtained in the reaction with the diol is transformed into 2- (4-methyl-phenyl) - [1,3,2] dioxaborolane, which is subjected to a free radical bromination reaction to obtain 2- (4-bromomethyl-phenyl) - [1, 3.2] dioxaborolate. 2- (4-chlorobenzylideneamino) -3-methyl-butanoic acid methyl ester obtained from D, L-valine by reaction with thionyl chloride and methanol is reacted with 4-chlorobenzoaldehyde to give an imine, which is converted by deprotonation to an imine anion and then reacted with 2- (4-bromomethyl-phenyl) - [1,3,2] dioxaborolate. The last step is treated with an inorganic acid to give the target 2-amino-2- (4-dihydroxyborylbenzyl) -3-methyl-butanoic acid methyl ester.

PL40549513A 2013-09-30 2013-09-30 2-amino-2-(4-dihydroxy boryl benzyl)-3-methylbutanoic acid metyl ester and method to produce it PL405495A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PL40549513A PL405495A1 (en) 2013-09-30 2013-09-30 2-amino-2-(4-dihydroxy boryl benzyl)-3-methylbutanoic acid metyl ester and method to produce it

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PL40549513A PL405495A1 (en) 2013-09-30 2013-09-30 2-amino-2-(4-dihydroxy boryl benzyl)-3-methylbutanoic acid metyl ester and method to produce it

Publications (1)

Publication Number Publication Date
PL405495A1 true PL405495A1 (en) 2015-04-13

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PL40549513A PL405495A1 (en) 2013-09-30 2013-09-30 2-amino-2-(4-dihydroxy boryl benzyl)-3-methylbutanoic acid metyl ester and method to produce it

Country Status (1)

Country Link
PL (1) PL405495A1 (en)

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