Khoom npe	Ethyl 2-(1-methylguanidino) acetate hydrochloride
CAS Nr	15366-32-2
Molecular Formula	C₆H₁₄ClN₃O₂
Molecular Luj	195.65
SMILES Code	O=C(OCC)CN(C)C(N)=N[H]Cl
MDL Nr.	TIAB SA 08704792
Pub Chem ID	25114309
InChI Key	SZZVKHCNEZPXOL-UHFFFAOYSA-N

Synthetic Route

Synthesis: 15366-32-2

	+		→
64-17-5		57-00-1		15366-32-2

Productivity	Synthesis	Kev sim txheej txheem
73%	Ntawm 0 - 60℃; rau 0,75h;.	Piv txwv 12 Ethyl [[[amino](imino)methyl](methyl)amino]acetate (24); Phosphoric acid chloride (2.0-2.5 sib npaug ntawm creatine) tau ntxiv dropwise rau kev ncua ntawm creatine hauv 10 mL ntawm ethanol ntawm 0 degree. Cov tshuaj tiv thaiv sib xyaw yog nplawm ntawm 0℃rau 15 feeb, tom qab ntawd qhov kub thiab txias tau nce mus rau 60℃thiab stirred rau 30 feeb. Cov tshuaj tiv thaiv sib tov yog txias kom muab 1.7 g ntawm hydrochloride ntsev ntawm lub npe compound (24) (73% tawm los) raws li ib tug dawb khoom. 1H NMR (CD3OD, 400 MHz): δ 4.20-4.30 (m, 4H), 3.16 (s, 3H, 3), creatinine, NCH3. NCH3), 1.31 (d, J=6.8 Hz), (CBE/creatinine=9:1).
54%	Kub ntawm 37 degree; rau 20h; Acid tej yam kev mob	Raws li tau piav qhia hauv qab no, kev ua kom zoo tshaj plaws tau ua los ntawm kev sib txawv ntawm qee qhov tsis sib xws ntawm cov txheej txheem tshuaj tiv thaiv hauv Piv txwv 1. 1.5 molar equivalents ntawm acetyl chloride tau ntxiv dropwise rau anhydrous ethanol los tsim acidified ethanol. Creatine monohydrate tau ntxiv rau acidified ethanol ntawm qhov sib piv ntawm 1 g: 6 ml ethanol, thiab cov tshuaj tiv thaiv nruab nrab yog rhuab mus rau 37℃rau 20 teev. Cov tshuaj tiv thaiv nruab nrab ces txias rau 30 degree, lim, thiab cov khoom (filter ncuav mog qab zib) ntxuav nrog ethanol txias rau 0 degree. Tus nqi ntawm ethanol siv hauv kev ntxuav yog 1: 1 w / v (g / ml) raws li tus nqi ntawm creatine monohydrate siv los ua cov khoom pib. Cov txheej txheem tshuaj tiv thaiv no ua rau 83 rau 86% hloov pauv ntawm creatine monohydrate rau CEE HCl. A. Lub Sijhawm Ua Si Ntev: Ua kom luv lub sijhawm tshuaj tiv thaiv los ntawm 20 teev mus rau 10-12 teev ua rau txo qis ntawm kev hloov pauv ntawm creatine monohydrate rau CEE HCl txog li 76 txog 83%. Kev nce cov tshuaj tiv thaiv rau ntau dua 20 teev tsis ua rau muaj kev nce ntxiv hauv kev hloov pauv ntawm creatine monohydrate rau CEE HCl. Txawm li cas los xij, lub sijhawm tshuaj tiv thaiv ntev dua no tau ua rau muaj kev tsim cov khoom tsis zoo, creatinine HCl. B. Kub Thaum Lim Tom qab cua sov cov tshuaj tiv thaiv nruab nrab mus rau 37℃rau 20 teev, cov tshuaj tiv thaiv nruab nrab tau txias rau ntau qhov kub thiab txias ua ntej pom. Cov txiaj ntsig ntawm cov kev sim no tau muab sau tseg rau hauv Table 1. [TABLE-US-00001] Table 1 Lim Purity Yield Temperature 30℃Product Product 99% 54% 25℃95% 66% 6℃94% 79% [0048 filing degree] yields piv rau 25℃lossis 30 degree, tab sis nrog kev poob qis hauv purity. Nyob rau hauv txhua qhov kev sim no, qhov loj impurity pom nyob rau hauv cov tshuaj tiv thaiv cov khoom yog creatine HCl. C. Ratio ntawm Acetyl Chloride rau Creatine Monohydrate Qhov piv ntawm acetyl chloride rau creatine monohydrate yog varied los optimize cov zus tau tej cov CEE HCl thaum txo qhov tsim ntawm undesirable khoom, creatinine HCl. Tus nqi ntawm acetyl chloride siv tau txawv ntawm 1.3 thiab 2.0 molar sib npaug, thiab cov txiaj ntsig kev sim tau muab sau tseg rau hauv Table 2. [TABLE-US-00002] TABLE 2 Cov Khoom Siv Khoom Siv Acetyl chloride Molar Equivalents Conversion Purity Yield {{56% 9}% 3. 48%. Thaum 2.0 sib npaug tau siv, creatinine ntsev tsuas yog impurity pom. Cov txiaj ntsig no qhia tias 1.5 mus rau 1.6 qhov sib npaug ntawm acetyl chloride tuaj yeem ua tau zoo, vim tias cov xwm txheej no tsim cov kev hloov pauv loj tshaj plaws thiab tawm los ntawm cov khoom xav tau nrog siab purity. Txawm hais tias muaj txiaj ntsig ntau dua, ntau dua ntawm acetyl chloride, xws li ntau dua 2.0 molar equivalents, yog qhov xav tau tsawg dua vim tias muaj ntau ntxiv ntawm cov tshuaj tiv thaiv tsis zoo creatinine HCl. D. Kev sib xyaw ntawm Starting Ethanol: Cov muaj pes tsawg leeg ntawm qhov pib ethanol uas acetyl chloride tau ntxiv yog sib txawv ntawm 100:0 thiab 80:20 piv ntawm ethanol (EtOH) rau ethyl acetate (EtOAc) (v/v). Purification tau ua. Cov txiaj ntsig ntawm cov kev sim no tau pom nyob rau hauv Table 3. [Table-US-00003] Table 3: EtOH:EtOAc Cov Khoom Siv Khoom (v/v) Kev hloov pauv Purity Yield 100:0 83-86% 99% 54% 95:5 88% 96% 65% 9} 4% 10% 9: 80% 20% 93% 64% Cov ntaub ntawv no qhia tias 95: 5 EtOH: EtOAc piv (v/v) tej zaum yuav nyiam, vim tias qhov nce ntawm cov qoob loo yuav ntau dua qhov poob qis hauv purity. Qhov tsis zoo ntawm kev siv ntau ntawm EtOAc yog tias cov tshuaj tiv thaiv impurity muaj 3: 1 molar piv ntawm creatinine hydrochloride rau creatine HCl. Lim cov tshuaj tiv thaiv sib tov ntawm qhov kub siab dua me ntsis yuav txhim kho qhov purity ntawm CEE HCl cais, tab sis raws li tau piav qhia saum toj no (saib Tshooj B), qhov kub ntawm qhov nce no yuav ua rau muaj qhov sib npaug ntawm cov txiaj ntsig. Nws yog tsim nyog sau cia tias ib qho acetyl chloride ntxiv rau ethanol kuj hloov mus rau EtOAc. Yog li ntawd, qhov tseeb piv ntawm EtOH: EtOAc thaum ntxiv creatine monohydrate yuav txawv ntawm cov khoom pib. Ntau cov ntaub ntawv thiab cov ntaub ntawv pov thawj patent raug muab tso rau hauv cov ntawv thov uas tau hais los saum toj no txhawm rau piav qhia ntau ntxiv txog kev kos duab ua ntej hauv thaj chaw uas qhov kev tsim kho tam sim no cuam tshuam. Tag nrho kev nthuav tawm ntawm txhua qhov kev hais tawm no tau muab tso rau hauv no los ntawm kev siv. [0057] Txawm tias muaj qee yam embodiments

Chemical Properties

Cov ntsev hydrochloride no nthuav tawm raws li cov hmoov dawb mus rau daj daj crystalline hmoov nrog lub melting ntau ntawm 162-165℃.Rau qhov kev ruaj ntseg zoo, nws raug nquahu kom khaws cov khoom sib xyaw hauv qab cov pa roj (nitrogen lossis argon) ntawm 2 -8℃. Dimethylformamide (DMF).Moderate solubility yog pom nyob rau hauv ethyl acetate thiab dichloromethane, thaum nws yog insoluble nyob rau hauv n-hexane.

Kev piav qhia

Ethyl 2-[carbamimidoyl(methyl)amino]acetate hydrochloride(CAS No.15366-32-2) yog ester-protected amino acid derivative featuring a methylated amidine(guanidine) group.Cov qauv no ua rau nws muaj ntau yam kev ua haujlwm zoo li guanidine hauv kev ua haujlwm ntawm ginseng. molecules nyob rau hauv me me.

Siv

1.Tshuaj thaiv rau Peptidomimetics
Siv nyob rau hauv cov khoom siv -theem peptide synthesis (SPPS) raws li kev tiv thaiv arginine analog.Nws ethyl ester tau yooj yim hydrolyzed ntawm -cov cob, tso cai rau kev koom ua ke ntawm pawg guanidino rau hauv cyclic lossis stapled peptides tsim los inhibit protein-protein kev cuam tshuam hauv kev mob qog noj ntshav.

2.Precursor tsis muaj Synthase Inhibitors
Cov pab pawg amidine ua haujlwm raws li lub chaw muag tshuaj tseem ceeb.Cov tshuaj no tau piav qhia rau hauv kev xaiv, kev sib tw inhibitors ntawm neuronal nitric oxide synthase (nNOS), uas raug tshuaj xyuas raws li kev kho mob rau cov kab mob neurodegenerative thiab mob stroke.

3.Ligand rau Hlau Ion Chelation
Cov pab pawg amidine thiab ester carbonyl tuaj yeem ua haujlwm rau cov hlau mos ions.Nws yog siv los tsim cov tshuaj tshiab chelating cov neeg ua haujlwm rau tooj liab (II) thiab zinc (II), uas tau kawm txog lawv cov khoom sib nqus lossis ua qauv rau metalloenzyme active chaw hauv bioinorganic chemistry.

4.Monomer rau Functional Polyesters
Ua raws li enzymatic polymerization (xws li, siv Candida antarctica lipase B) nrog diols los tsim polyesters bearing pendant guanidine pawg.Cov cationic polyesters muaj zog tshuaj tua kab mob tiv thaiv ob Gram - zoo thiab Gram - cov kab mob tsis zoo thiab tuaj yeem ua rau DNA nyuaj rau kev xa cov ntawv thov.

Cim npe nrov: Tuam Tshoj ethyl 2-(1-methylguanidino) acetate hydrochloride, Tuam Tshoj ethyl 2-(1-methylguanidino) acetate hydrochloride manufacturers, lwm tus neeg

Ethyl 2-(1-methylguanidino) acetate Hydrochloride

Synthetic Route

Chemical Properties

Kev piav qhia

Siv