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 itInfo
- 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
Links
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.
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
ID=52781905
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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2013
- 2013-09-30 PL PL40549513A patent/PL405495A1/en unknown
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