EP 3319946 A1 20180516 - METHOD FOR THE SYNTHESIS OF 2,6-BIS (METHIONYL) -1,4-DIKETOPIPERAZINE
Title (en)
METHOD FOR THE SYNTHESIS OF 2,6-BIS (METHIONYL) -1,4-DIKETOPIPERAZINE
Title (de)
VEREINFACHTES UND SKALIERFÄHIGES VERFAHREN ZUR SYNTHESE VON 2,6-BIS(METHIONYL)-1,4-DIKETOPIPERAZIN
Title (fr)
PROCEDE DESTINE A LA SYNTHESE DE 2,6-BIS (METHIONYL)-1,4-DICETOPIPERAZINE
Publication
Application
Priority
- EP 15176058 A 20150709
- EP 2016064982 W 20160628
Abstract (en)
[origin: WO2017005547A1] The invention relates to a method for producing 2,6-bis(methionyl)-1,4-diketopiperazine comprising the following steps: a) heating a reaction mixture containing methionine and a polar protic solvent at a temperature of 145.0 to 169.5 °C, wherein an inert gas flow is directed over or through the reaction mixture; b) obtaining 2,6-bis(methionyl)-1,4-diketopiperazine. The invention further relates to a method for isolating 2,6-bis(methionyl)-1,4-diketopiperazine from a reaction mixture, comprising the following steps: A1) diluting the reaction mixture containing 2,6-bis(methionyl)-1,4-diketopiperazine using a polar solvent and water, wherein 2,6-Bis(methionyl)-1,4-diketopiperazine crystallises; or A2) diluting the reaction mixture containing 2,6-bis(methionyl)-1,4-diketopiperazine using water only, without prior diluting with an organic solvent and with or without pressure control, wherein 2,6-bis(methionyl)-1,4-diketopiperazine crystallises; or A3) cooling the reaction mixture, or allowing same to cool, without the addition of substances until a temperature is reached, in particular of 135.0 to less than 145.0 °C, preferably 138.0 to 142.0 °C, at which the diketopiperazine begins to crystallise, and finally diluting by the addition of water and resultant cooling, wherein 2,6-bis(methionyl)-1,4-diketopiperazine crystallises; B) separating the crystallised 2,6-bis(methionyl)-1,4-diketopiperazine obtained as a solid in A1) or A2) or A3) and washing with a solvent, in particular ethylene glycol, acetone or methanol, and finally washing with water. The present invention relates in particular to a combination of a method for producing 2,6-bis(methionyl)-1,4-diketopiperazine and a method for isolating 2,6-bis(methionyl)-1,4-diketopiperazine from a reaction mixture.
IPC 8 full level
C07D 241/00 (2006.01); C07K 5/062 (2006.01)
CPC (source: EP US)
C07D 241/08 (2013.01 - EP US); C07K 5/12 (2013.01 - US); C07K 5/0606 (2013.01 - EP US)
Citation (search report)
See references of WO 2017005547A1
Designated contracting state (EPC)
AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR
Designated extension state (EPC)
BA ME
DOCDB simple family (publication)
WO 2017005547 A1 20170112; CN 107922355 A 20180417; CN 107922355 B 20201215; EP 3319946 A1 20180516; JP 2018521065 A 20180802; RU 2018104882 A 20190809; SG 11201800148V A 20180227; US 2018194804 A1 20180712
DOCDB simple family (application)
EP 2016064982 W 20160628; CN 201680046910 A 20160628; EP 16733932 A 20160628; JP 2018500397 A 20160628; RU 2018104882 A 20160628; SG 11201800148V A 20160628; US 201615741846 A 20160628