PL411939A1 - Methyl ester of 2-amino-2-(4-dihydroxyboryl benzyl)-3-methylbutanoic acid and method for obtaining it - Google Patents
Methyl ester of 2-amino-2-(4-dihydroxyboryl benzyl)-3-methylbutanoic acid and method for obtaining itInfo
- Publication number
- PL411939A1 PL411939A1 PL411939A PL41193915A PL411939A1 PL 411939 A1 PL411939 A1 PL 411939A1 PL 411939 A PL411939 A PL 411939A PL 41193915 A PL41193915 A PL 41193915A PL 411939 A1 PL411939 A1 PL 411939A1
- Authority
- PL
- Poland
- Prior art keywords
- organic solvent
- methyl ester
- amino
- low temperature
- acid methyl
- Prior art date
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Abstract
Ujawniono ester metylowy kwasu 2-amino-2-(4-dihydroksy-borylobenzylo)-3-metylobutanowego jako nowy boronowany aminokwas z zabezpieczoną grupą karboksylową w postaci estru metylowego, z izopropylowym podstawnikiem przy ?-atomie węgla o wzorze (I) oraz sposób wytwarzania estru metylowego kwasu 2-amino-2-(4-dihydroksyborylobenzylo)-3-metylobutanowego charakteryzuje się tym, że związkami wyjściowymi są D,L-walina i 4-bromotoluen, przy czym D,L-walinę poddaje się reakcji z chlorkiem tionylu i metanolem, w obniżonej temperaturze a otrzymany ester metylowy kwasu 2-(4-chlorobenzylidenoamino)-3-metylo-butanowego poddaje się następnie reakcji z aldehydem 4-chlorobenzoesowym w organicznym rozpuszczalniku, w obecności trietyloaminy oraz bezwodnego siarczanu magnezu, a uzyskaną iminę (2, 1e) przekształca się w reakcji czynnikiem deprotonującym w organicznym rozpuszczalniku, w niskiej temperaturze i atmosferze gazu obojętnego w anion iminy, który poddaje się reakcji w organicznym rozpuszczalniku, niskiej temperaturze i atmosferze gazu obojętnego z 2-(4-bromometylo-fenylo)-[1,3,2]dioksaborolanem (5, 1c), otrzymanym z 4 bromotoluenu w wyniku kolejnych reakcji; metalacji - transmetalacji z pochodną litoorganiczną w bezwodnym rozpuszczalniku organicznym, w niskiej temperaturze, a następnie reakcji z estrem triizopropylowym kwasu borowego w bezwodnym rozpuszczalniku organicznym, w niskiej temperaturze, w atmosferze gazu obojętnego i kwasowej hydrolizie, a otrzymany 4-dihydroksyborylotoluen (3, 1a), poddaje się reakcji z diolem w bezwodnym organicznym rozpuszczalniku, w temperaturze pokojowej, który przekształca się w 2-(4-metylo-fenylo)-[1,3,2] dioksaborolan (4, 1b), a otrzymany ester poddaje się reakcji wolnorodnikowego bromowania w bezwodnym rozpuszczalniku organicznym, w podwyższonej temperaturze otrzymując 2-(4-bromometylo-fenylo)-[1,3,2] dioksaborolan (5, 1c), a po zakończeniu reakcji w niskiej temperaturze działa kwasem nieorganicznym, uzyskując docelowy ester metylowy kwasu 2-amino-2-(4-dihydroksyborylobenzylo)-3-metylobutanowego (o wzorze 1).Disclosed 2-amino-2- (4-dihydroxy-borylbenzyl) -3-methylbutanoic acid methyl ester as a new boronated carboxyl protected amino acid methyl ester with an isopropyl substituent on the α-carbon of formula (I) and a method of preparation 2-amino-2- (4-dihydroxyborylbenzyl) -3-methylbutanoic acid methyl ester is characterized in that the starting compounds are D, L-valine and 4-bromotoluene, where D, L-valine is reacted with thionyl chloride and methanol, at a reduced temperature, and the obtained 2- (4-chlorobenzylideneamino) -3-methyl-butanoic acid methyl ester is then reacted with 4-chlorobenzoaldehyde in an organic solvent in the presence of triethylamine and anhydrous magnesium sulfate, and the resulting imine (2, 1e) is transformed by reaction with a deprotonating agent in an organic solvent, at a low temperature and inert gas atmosphere, into an imine anion, which is reacted in an organic solvent, low temperature and an inert atmosphere with 2- (4-bromomethyl-phenyl) - [1,3,2] dioxaborolate (5, 1c), obtained from 4 bromotoluene by subsequent reactions; metallization - transmetalation with an organolithium derivative in an anhydrous organic solvent at a low temperature, followed by reaction with a boric acid triisopropyl ester in an anhydrous organic solvent, at a low temperature, under an inert gas atmosphere and acid hydrolysis, and the resulting 4-dihydroxyboryltoluene (3, 1a) , is reacted with a diol in an anhydrous organic solvent at room temperature, which is converted into 2- (4-methyl-phenyl) - [1,3,2] dioxaborolane (4,1b), and the resulting ester is subjected to a free radical reaction bromination in an anhydrous organic solvent, at elevated temperature to obtain 2- (4-bromomethyl-phenyl) - [1,3,2] dioxaborolate (5, 1c), and after completion of the reaction at low temperature, it acts with an inorganic acid to obtain the target acid methyl ester 2-amino-2- (4-dihydroxyborylbenzyl) -3-methylbutane (of formula 1).
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PL411939A PL227525B1 (en) | 2015-04-10 | 2015-04-10 | Methyl ester of 2-amino-2-(4-dihydroxyboryl benzyl)-3-methylbutanoic acid and method for obtaining it |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PL411939A PL227525B1 (en) | 2015-04-10 | 2015-04-10 | Methyl ester of 2-amino-2-(4-dihydroxyboryl benzyl)-3-methylbutanoic acid and method for obtaining it |
Publications (2)
Publication Number | Publication Date |
---|---|
PL411939A1 true PL411939A1 (en) | 2016-10-24 |
PL227525B1 PL227525B1 (en) | 2017-12-29 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PL411939A PL227525B1 (en) | 2015-04-10 | 2015-04-10 | Methyl ester of 2-amino-2-(4-dihydroxyboryl benzyl)-3-methylbutanoic acid and method for obtaining it |
Country Status (1)
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PL (1) | PL227525B1 (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
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CN117545759A (en) * | 2021-06-25 | 2024-02-09 | 斯特拉制药公司 | Derivatives of dihydroxyborylphenylalanine |
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2015
- 2015-04-10 PL PL411939A patent/PL227525B1/en unknown
Also Published As
Publication number | Publication date |
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PL227525B1 (en) | 2017-12-29 |
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