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 it

Info

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
Application number
PL411939A
Other languages
Polish (pl)
Other versions
PL227525B1 (en
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 PL411939A priority Critical patent/PL227525B1/en
Publication of PL411939A1 publication Critical patent/PL411939A1/en
Publication of PL227525B1 publication Critical patent/PL227525B1/en

Links

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).

PL411939A 2015-04-10 2015-04-10 Methyl ester of 2-amino-2-(4-dihydroxyboryl benzyl)-3-methylbutanoic acid and method for obtaining it PL227525B1 (en)

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

ID=57821584

Family Applications (1)

Application Number Title Priority Date Filing Date
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)

Country Link
PL (1) PL227525B1 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117545759A (en) * 2021-06-25 2024-02-09 斯特拉制药公司 Derivatives of dihydroxyborylphenylalanine

Also Published As

Publication number Publication date
PL227525B1 (en) 2017-12-29

Similar Documents

Publication Publication Date Title
Kadam et al. Comparative performance evaluation and systematic screening of solvents in a range of Grignard reactions
AR063449A1 (en) CHEMICAL PROCESS FOR QUINAZOLINE DERIVATIVES, INTERMEDIARIES
JP2013199502A5 (en)
JP2013533231A5 (en)
BR112014018756A8 (en) PROCESS FOR PREPARING N-(4-CYCLO-HEXYL-3-TRIFLUOROMETHYL-BENZYLOXY)-ACETIMIDIC ACID ETHYL ESTER
AR103230A1 (en) PROCESSES FOR THE PREPARATION OF A DIARILTIOHIDANTOINE COMPOUND
AR117002A2 (en) PROCESS FOR THE PREPARATION OF KINASE C-FMS INHIBITORS
MX2020006306A (en) Novel method for producing 5,5-disubstituted-4,5-dihydroisoxazole .
MX2014006992A (en) Malonic acid di-salts and a method for preparing malonyl dihalides.
CY1121415T1 (en) IMPROVED METHOD FOR MEYLTANSINOL ACHYLATION
EA201490998A1 (en) METHOD OF OBTAINING COMPLEX ETHERS (5-FLUOR-2-METHYL-3-QUINOLIN-2-ILMETHIL-INDOL-1-IL) -CATTY ACID
WO2012099736A3 (en) Improved process for preparation of high molecular weight molybdenum succinimide complexes
ES2541857T3 (en) Processes for preparing cyclopropylamides and intermediates associated with these
PL411939A1 (en) Methyl ester of 2-amino-2-(4-dihydroxyboryl benzyl)-3-methylbutanoic acid and method for obtaining it
AR049663A1 (en) PREPARATION PROCESS OF USEFUL AMINO ACIDS IN THE PREPARATION OF MODULATORS OF THE PEPTIDE RECEIVER
MX2015016957A (en) Synthesis of dicarbamates from reduction products of 2-hydroxymethyl-5-furufural (hmf) and derivatives thereof.
IN2014CN02346A (en)
WO2015143019A3 (en) Gaseous f-18 technologies
UA117849C2 (en) Process for the preparation of 3-substituted (indol-1-yl)-acetic acid esters
TN2014000329A1 (en) Method for preparing compound by novel michael addition reaction using water or various acids as additive
UY33342A (en) PROCESS FOR THE PREPARATION OF AMIDAS OF CARBOXYL ACID PIRAZOL
AR077332A1 (en) PROCESSES FOR THE RENTAL OF PIRAZOLES
PL405495A1 (en) 2-amino-2-(4-dihydroxy boryl benzyl)-3-methylbutanoic acid metyl ester and method to produce it
PH12019500484A1 (en) Optimized production method for pest control agent
EA201400563A1 (en) METHOD OF OBTAINING QUINOLINCARBONIC ACID