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CAS No. : | 7200-25-1 | MDL No. : | MFCD00063117 |
Formula : | C6H14N4O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 174.20 | Pubchem ID : | - |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.67 |
Num. rotatable bonds : | 6 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 5.0 |
Molar Refractivity : | 44.53 |
TPSA : | 125.22 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -10.34 cm/s |
Log Po/w (iLOGP) : | -0.31 |
Log Po/w (XLOGP3) : | -4.2 |
Log Po/w (WLOGP) : | -1.34 |
Log Po/w (MLOGP) : | -3.21 |
Log Po/w (SILICOS-IT) : | -1.61 |
Consensus Log Po/w : | -2.13 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | 2.12 |
Solubility : | 23100.0 mg/ml ; 132.0 mol/l |
Class : | Highly soluble |
Log S (Ali) : | 2.18 |
Solubility : | 26200.0 mg/ml ; 150.0 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | 0.06 |
Solubility : | 200.0 mg/ml ; 1.15 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.16 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H319 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With chiral stationary phase including isopropyl-functionalized CF6; In ethanol; n-heptane; trifluoroacetic acid; at 20℃;Purification / work up; | In addition to the foregoing, numerous other chromatographic separations using a column bonded with a CSP including a derivatized cyclofructan residue were carried out. Tables 5-9 list some additional examples of chromatographic separations using a column bonded with a CSP of the present invention. AU examples of chromatographic separations using columns bonded with CSPs of the present invention were carried out using the following experimental conditions and procedures.|0132| The high performance liquid chromatography (HPLC) column packing system was composed of an air driven fluid pump (HASKEL, DSTV- 122), an air compressor, a pressure regulator, a low pressure gauge, two high-pressure gauges (10,000 and 6,000 psi), a slurry chamber, check valves, and tubings. The CSPs were slurry packed into a 25 cm x 0.46 cm (inner diameter, I. D.) stainless steel column.|0133| The HPLC system was an Agilent 1 100 system (Agilent Technologies, Palo Alto,CA), which consisted of a diode array detector, an autosampler, a binary pump, a temperature- controlled column chamber, and Chemstation software. All chiral analytes were dissolved in ethanol, methanol, or other appropriate mobile phases, as indicated. For the LC analysis, the injection volume and flow rate were 5 muL and 1 mL/min, respectively. Separations were carried out at room temperature (~20 0C) if not specified otherwise. The wavelengths of UV detection were 195, 200, 210, and 254 nm. The mobile phase was degassed by ultrasonication under vacuum for 5 min. Each sample was analyzed in duplicate. Three operation modes (the normal phase mode, polar organic mode, and reversed phase mode) were tested, unless indicated otherwise. In the normal phase mode, heptane with ethanol or isopropanol was used as the mobile phase. In some cases, trifluoroacetic acid (TFA) was used as an additive, as indicated. The mobile phase of the polar organic mode was composed of acetonitrile/methanol and small amounts of acetic acid and triethylamine. Water/acetonitrile or acetonitrile/acetate buffer (20 mM, pH = 4.1 ) was used as the mobile phase in the reversed-phase mode.|0134| Two different supercritical fluid chromatographic instruments were used. One was a Berger SFC unit with an FCM 1200 flow control module, a TCM 2100 thermal column module, a dual pump control module, and a column selection valve. The flow rate was 4 mL/min. The cosolvent was composed of methanol/ethanol/isopropanol = 1 : 1 : 1 and 0.2% diethylamine (DEA). The gradient mobile phase composition was 5% cosolvent hold during 0- 0.6 min, 5-60% during 0.6-4.3 min, 60% hold during 4.3-6.3 min, 60%-5% during 6.3-6.9 min, and 5% hold during 6.9-8.0 min. The other SFC system was a Jasco (MD, USA) system comprised of an autosampler unit (AS-2059-SF Plus), a dual pump module (PU-2086 Plus), a column thermostat module (CO-2060 Plus), a UV/Vis detector (UV-2075 Plus), and a back pressure regulator module (SCH-Vch-BP). Unless otherwise specified, the mobile phase was composed of CCVmethanol (0.1 % TFA or 0.1% diethylamine). The flow rate was 3 mL/min.|0135| For the calculations of chromatographic data, the "dead time" to was determined by the peak of the refractive index change due to the sample solvent or determined by injecting l ,3,5-tri-/e/-/-butylbenzene in the normal phase mode. | |
Separation Between the D-Body and L-Body of <strong>[7200-25-1]Arg</strong>inine (<strong>[7200-25-1]Arg</strong>)20 muL of a 200 mM (pH 8.0) buffer solution of sodium borate with a pH of 8.0 and 5 muL of a 40 mM solution of 4-fluoro-7-nitro-2,1,3-benzoxadiazole in anhydrous methyl cyanide were added to 50 pmol of a mixture of the D-body and the L-body of <strong>[7200-25-1]Arg</strong>inine with a mass ratio of 1:4, and subsequently, heating was conducted at 60 C. for 2 minutes to cause fluorescent derivatization thereof. Then, 95 muL of a 0.5% aqueous solution of trifluoroacetic acid was added thereto, so that a measurement sample was obtained.The column was mounted on a high performance liquid chromatograph SI-2 (produced by Shiseido Co., Ltd.), and subsequently, 2 muL of the measurement sample was injected thereto on the following conditions, so that the D-body and the L-body of arginine were separated.Temperature: 25 C.Mobile phase: methanol Flow rate of the mobile phase: 150 L/min |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | In methanol; at 20 - 40℃; for 20h; | Example79 <strong>[7200-25-1]Arg</strong>enine salt of 2-{4-[3-(l,5-dimethyl-7-oxo-3-propyl-l,7-dihydro-pyrazolo[4,3- d]pyrimidin-6-yl)-propyl]-phenoxy}-2-methyI-propionic acid; The title compound was prepared by treating 2-{4-[3-(l,5-dimethyl-7-oxo-3- propyl-l,7-dihydro-pyrazolo[4,3-d]pyrimidin-6-yl)-propyl]-phenoxy}-2-methyl- propionic acid (145 mg, 0.34 mmol), obtained in example 78, in methanol (3 mL) and argenine (59 mg, 0.34 mmol) at 20 to 40 0C for 20 hours. Yield: 190 mg, 93%. Melting Point: 104-106 0C 1H NMR (CDCl3, 200 MHz): delta 7.09 (d, J = 8.9 Hz, 2H), 6.85 (d, J = 8.4 Hz, 2H), 4.17 (s, 3H), 4.07 (t, J = 8.0 Hz, 2H), 3.22-3.14 "(m, 3H), 2.79 (t, J = 7.5 Hz, 2H), 2.67 (t, J = 7.6 Hz,- 2H), 2.48 (s, 3H), 2.35 (t, J = 6.5 Hz, IH), 2.06-1.95 (m, 2H), 1.85-1.62 (m, 6H), 1.50 (s, 6H), 0.96 (t, J = 7.4 Hz, 3H). Mass (CI): m/z 601.5 (M++l). IR (cm-1) (KBr): 2963, 1685, 1572, 1509. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; for 0.0666667h;pH 9.2 - 11.5; | First Process for Preparing 2-amino 5-triaminoguanidovalericbenzoicdiacetate; C15H28N6O6 ; Intermediate Reaction Product,2-amino 5-diaminoguanidovalericdiacetate; C8H19N5O4 ; 2-amino 5-diaminoguanidovalericdiacetate is an intermediate reaction product and is a unique molecule useful in releasing free amino ions, which because of weak internal hydrogen bonding, then allows for the release of the amino ions. While in aqua's solution these ions provide numerous and various positive physiological effects in both humans and animals such as stabilizing unstable nucleic acids within dysfunctional cells by process of biosynthesis. This reaction product may also be used to boost and accelerate topical microcirculation and is also useful in the manufacture of other reaction products that allows for release of a greater quantity of free amino ions when in aqua's solution to further achieve more effective and positive physiological effects such as the above stated stabilization of unstable nucleic acids within dysfunctional cells by means of biosynthesis.To obtain 2-amino 5-diaminoguanidovalericdiacetate, those skilled in the art will dissolve at ultra high shear and at 80 degrees Centigrade, 227.0 Grams of 2-amino 5-aminoguanido valaric acid in 1 liter of de-ionized water (USP). The ultra high shear mixing should take at least four minutes. Applicant uses a Ross homogenizer; however a Fischer PowerGen Model 1800D homogenizer would work satisfactorily. The mixing speed should be at least 4,000 rpm. The resulting solution should have PH of about 11.5. Reduce the mixing speed to 300 rpm and add 183.0 Grams of aminoacetic acid. Gradually increase mixing speed to 4000 rpm and mix at this speed for at least four minutes. PH should be about 9.2 but will rise to about 9.3 as solution cools.A drawing of the chemical structure of this molecule is shown in FIG. 3. This solution of 2-amino 5-diaminoguanidovalericdiacetate may then be used to achieve the final reaction product, namely 2-amino 5-triaminoguanidovalericbenzoicdiacetate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; at 20 - 80℃; for 0.1h;pH 8.2 - 9.03;Product distribution / selectivity; | Final Reaction Product; 2-amino 5-triaminoguanidovalericbenzoicdiacetate; To obtain the final product, 2-amino5-triaminoguanidovalericbenzoicdiacetate using the diaminobenzoicdiacetate, add to the diaminobenzoicdiacetate solution at 80 degrees Centigrade 227.0 Grams of 2-amino5-aminoguanidovaleric acid (arginine). Gradually increase mixing speed to 3000 rpm and mix at this speed for at least three minutes. PH will be 9.0 but will rise to 9.03 as solution cools to room temperature. Return temperature to 80 degrees C. and add 25 Grams of 4-aminobenzoic acid again, mixing at 3000 rpm for at least three minutes. The resulting PH should be 8.2 rising to 8.5 as the mixture cools to room temperature. This is a satisfactory end point resulting in the final product, i.e. 2-amino 5-triaminoguanidovalericbenzoicdiacetate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water;pH 9; | a) Preparation of 4,26-diamino-5,10,15,20-tetracarbonyl-12,15,18-tricarboxymethyl-6,9,12,15,18,21,24-heptaazanonaheicosan-1,29-diguanidina. 2-amino-5-guanidino-valeric acid (arginine, 0.871 g; 0.005 mol) is dissolved in an aqueous solution at pH 9 and a strong excess of benzyl chloroformate is then slowly added thereto. The thus obtained corresponding tri-carbobenzyloxy derivative is isolated, dissolved in methylene chloride and added with di-cyclohexylcarbodiimide. Theobtained solution is then slowly added to a solution of ethylenediamine (1.5 g; 0.025 mol) in methylene chloride. The2-aminoethylamide of the tri-carbobenzyloxy protected arginine is recovered, dissolved in DMSO and a solution ofdiethylentriaminopentaneacetic acid bis-anhydride (1.78 g; 0.005 mol) in DMSO is then added to the obtained solutionheated to 50 C. The reaction mixture is stirred at this temperature for 4 hours and then cooled to room temperature.The pH is adjusted to 8 by the addition of methanolic KOH and the raw product that precipitates is washed with acetone under stirring overnight. The solid is then recovered, dissolved in methanol and the protecting carbobenzyloxy groups are removed by catalytic hydrogenation over Pd/C 5 %. Any residual carbamic acid that may possibly be present is then removed by acidification with HCl yielding the desired compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; | 300 mg of estramustine phosphate were weighed in a beaker and dispersed by means of magnetic stirring in 5 ml of water. 101 mg of arginine base were then added to the watery dispersion of the active whilst maintaining under stirring until a clear solution was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; | 300 mg of estramustine phosphate were weighed in a beaker and dispersed by means of magnetic stirring in 5 ml of water. 202 mg of arginine base were then added to the watery dispersion of the active whilst maintaining under stirring until a clear solution was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; acetonitrile; at 20℃; for 2h; | Cbz-Phe-Pro-BoroMpg-OH obtained by the method of Example 5 (20.00g, 38. 1mM) is dissolved in acetonitrile (200moi) with stirring at room temperature. To this solution is added arginine as a 0.2M solution in distilled water (190ml). The resultant clear solution is stirred for 2 hours at room temperature and then evacuated to dryness under vacuum with its temperature not exceeding 37C. The resultant oil/tacky liquid is redissolved in 2L distilled water with warming to 37C for 2 hours. The solution is filtered through filter paper and evacuated to dryness, again with the temperature of the solution not exceeding 37C. The resultant product is dried under vacuum overnight to normally yield a white brittle solid. The salt was then dried under vacuum over silica to constant weight (72 h). Yield : 10. 54g. Microanalysis : C % Found H % Found N % Found B % Found (Calc.) (Calc.) (Calc.) (Calc.) 52. 47 7. 12 15. 25 1. 52 (56.65) (7.20) (14.01) (1-54) | |
In water; acetonitrile; at 20℃; for 2h; | Cbz-Phe-Pro-BoroMpg-OH obtained by the method of Example 5 (20.00g, 38. 1mM) is dissolved in acetonitrile (200moi) with stirring at room temperature. To this solution is added arginine as a 0.2M solution in distilled water (190ml). The resultant clear solution is stirred for 2 hours at room temperature and then evacuated to dryness under vacuum with its temperature not exceeding 37C. The resultant oil/tacky liquid is redissolved in 2L distilled water with warming to 37C for 2 hours. The solution is filtered through filter paper and evacuated to dryness, again with the temperature of the solution not exceeding 37C. The resultant product is dried under vacuum overnight to normally yield a white brittle solid. The salt was then dried under vacuum over silica to constant weight (72 h). Yield : 10. 54g. Microanalysis : C % Found H % Found N % Found B % Found (Calc.) (Calc.) (Calc.) (Calc.) 52. 47 7. 12 15. 25 1. 52 (56.65) (7.20) (14.01) (1-54) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; water; | A solution of 2-acetyl-5- (5-nitroxypentanoyl)benzoicacid in ethanol was added to a hydroalcoholic solution of EPO <DP n="17"/>arginine. After evaporation of the solvent, the productwas dissolved in water and the resulting solution wasdivided in vials of 1.5 ml each and lyophilised for 14hours. Water content (K.F.) < 2%.In the same way, the corresponding salt of agmatinewas obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With phosphoric acid; iodine; In water; | EXAMPLE 3 Preparation of arginine iodine Following a method similar to example 1, 150 ml of water was added, raised the temperature up to 80 C. with stirring, then added 10 g of L-arginine, when dissolved completely, 1.5 g of phosphoric acid was added, and 4.4 g of iodine was then introduced gradually, and the mixture was stirred for about 110 minutes, cooled and stood for about 180 minutes, then filtrated, the filtrate was concentrated and dried to afford 13.70 g title compound. By analyzing, the obtained product was found to have the following data: Available iodine content: 4.0 g <strong>[7200-25-1]Arg</strong>inine:9.6 g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | In methanol; at 20 - 40℃; for 20h; | Example 82 <strong>[7200-25-1]Arg</strong>enine salt of 2-{3-[3-(l,5-dimethyl-7-oxo-3-propyI-l,7-dihydro-pyrazolo[4,3- d]pyrimidin-6-yl)-propyl]-phenoxy}-2-methyl-propionic acid; The title compound was prepared by treating 2-{3-[3-(l,5-dimethyl-7-oxo-3- propyl-l,7-dihydro-pyrazolo[4,3-d]pyrimidin-6-yl)-propyl]-phenoxy}-2-methyl- propionic acid (95 mg, 0.223 mmol), obtained in example 81, in methanol (2 mL) and argenine (38 mg, 0.223 mmol) at 20 to 40 C for 20 hours. Yield: 119 mg, 89%. Melting Point: 78-80 0C. 1H NMR (CD3OD, 400 MHz): delta 7.11 (d, J = 7.8 Hz, IH), 6.82-6.74 (m, 3H), 4.17 (s, 3H), 4.10-4.07 (m, 2H), 3.49 (t, J = 6.0 Hz, IH), 3.29-3.14 (m, 2H), 2.78 (t, J = 7.5 Hz, 2H), 2.69 (t, J = 7.4 Hz, 2H), 2.48 (s, 3H), 2.02-1.82 (m, 2H), 1.79-1.71 (m, 2H), 1.71- 1.66 (m, 4H), 1.50 (s, 6H), 0.96 (t, J = 7.4 Hz, 3H). Mass (ES): m/z 601.7 (M++l). IR (Cm"1) (Neat): 2925, 1690, 1573. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In methanol; at 20 - 40℃; for 20h; | Example85 <strong>[7200-25-1]Arg</strong>enine salt of 2-{4-[3-(5-ethyl-l-methyl-7-oxo-3-propyl-l,7-dihydro-pyrazolo[4,3- d]pyrimidin-6-yl)-propyl]-phenoxy}-2-methyl-propionic acid; The title compound was prepared by treating 2-{4-[3-(5-ethyl-l-methyl-7-oxo-3- propyl- 1 ,7-dihydro-pyrazolo[4,3-d]pyrimidin-6-yl)-propyl]-phenoxy} -2-methyl- propionic acid (36 mg, 0.08 mmol), obtained in example 84, in methanol (2 mL) argenine (14 mg, 0.08 mmol) was added and the reaction mixture was stirred at 20 to 40 C for 20 hours. Yield: 48 mg, 96%. Melting Point: 100-102 0C 1H NMR (CD3OD, 400 MHz): delta 7.08 (d, J = 8.6 Hz, IH), 6.86 (d, J = 8.6 Hz, 2H), 4.17 (s, 3H), 4.09-4.04 (m, 2H), 3.51 (t, J = 6.2 Hz, IH), 3.26-3.13 (m, 2H), 2.80 (t, J = 7.4 Hz, 2H), 2.71-2.65 (m, 4H), 2.00-1.95 (m, 2H), 1.82 (t, J = 6.9 Hz, 2H), 1.77 (t, J = 7.5 Hz, 2H), 1.73-1.68 (m, 4H), H), 1.49 (s, 6H), 1.26-1.22 (m, 3H), 0.96 (t, J = 7.4 Hz, 3H). IR (Cm-1) (KBr): 2931, 1685, 1555. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.065 g (91%) | EXAMPLE 6 2,8-Diaminooctanoic acid monohydrochloride (8) 2,8-Diaminooctanoic acid monohydrochloride (8) was prepared in manner similar to Example 5. Yield: 1.065 g (91%). Mp 276-277 C., monohydrochloride (lit mp 226-229 C. for dihydrochloride). TLC: Rf =0.28 (D), 0.10 (C). MW calc 174.14, found 174. Anal. calc for C8 H18 N2 O2 HCl: C, 45.60; H, 9.09. N, 13.29; Cl, 16.83. Found: C, 45.30; H, 9.29; N, 13.12; Cl, 17.11. HPLC 99%. 1 H-NMR (D2 O) 1.40 (6H, m), 1.68 (2H, m), 1.85 (2H, m), 3.00 (2H, t, 7 Hz), 3.75 (1H, t, 7 Hz). Spinco analysis: single peak with elution time equivalent to arginine. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 1,4-dioxane; N-methyl-acetamide; water; ethyl acetate; | I. BENZYLOXYCARBONYL-PROLYL-ARGININE To a solution of 37 g (0.1 mol) of p-nitrophenyl ether of benzyloxycarbonylproline in 360 ml of dioxane there is added a solution of 16 g (0.09 mole) of arginine in 160 ml of water under vigorous stirring. After two hours the solvent is evaporated and the residue is dissolved in 100 ml of dimethylformamide. The solution is stirred at room temperature (25 C.) for 72 hours and then poured into 1 liter of ethylacetate. After residence of the reaction mixture for 12 hours in a cooler the resulting precipitate is filtered-off, washed on the filter with ethylacetate and diethyl ether. After recrystallization of the product from a mixture of ethanol-diethyl ether (1:5) there are obtained 35 g (96%) of benzyloxycarbonyl-prolyl-arginine having the following properties: melting point 137-140 C., [L]D20 -46.6 (c 1.0; H2 O); Rf 0.53 (A, "Eastman"); 0.66 (B, "Eastman"), Ehis 0.56 (pH 2.4). Found, % by weight: C 53.17; H 6.08; N 15.91. Calculated for C19 H27 N5 O5.H2 O, % by weight: C 56.28; H 6.71; N 17.27. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; | EXAMPLE 7 L.arginine p.chlorohippurate A concentrated solution of L.arginine is made from 20 g L.arginine and 135 ml water. 127 g of this solution and 21.37 g p.chlorohippuric acid are mixed together. The whole mixture is stirred for one hour and thereafter evaporated off to dryness. The crude L.arginine p.chlorohippurate weighing 42.3 g is further purified. The crude product is taken up with 300 ml water. To this solution, arginine is added very carefully until the pH reaches the value of 7.2. The clear solution is then evaporated off. 32.7 g of L.arginine p.chlorohippurate are recovered and dried on phosphoric anhydride. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydrogencarbonate; In water; ethyl acetate; isopropyl alcohol; acetone; | [1] <strong>[7200-25-1]Arg</strong>inine-methacrylamide [compound represented by Formula (7)] Potassium hydrogencarbonate(27.64 g) was dissolved in 200 ml of distilled water, 21.07 g of arginine hydrochloridewas dissolved in the solution, and 80 ml of acetone was further added to the solution. The reaction mixture was added dropwise with 10.46 g of methacryloyl chloride over about 10 minutes with vigorous stirring under ice cooling, and further vigorously stirred for 1 hour. The reaction mixture was adjusted to pH 1 with concentrated hydrochloric acid, and saturated with sodium chloride. The aqueous layer was washed 3 times with 300 ml of ethyl acetate, and extracted 3 times with 200 ml of ethyl acetate/isopropanol = 1/1. The ethyl acetate/isopropanol layers were combined, concentrated to about 100 ml under reduced pressure, added with 400 ml of isopropanol, and again concentrated to about 200 ml. The deposited sodium chloride was removed by filtration, and the filtrate was concentrated (colorless syrup, 21.80 g) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With formic acid; acetic anhydride; In water; | (35) An oily 3-(N-formyl-N-hydroxyamino)propylphosphonic acid was obtained from 3-(N-hydroxyamino)propylphosphonic acid (9.30 g.) and a mixture of acetic anhydride (7.4 ml.) and formic acid (6.0 ml.) in substantially the same manner as that of Example (34). This oil was dissolved in water (70 ml.) to form a clear solution (81 ml.), of which an aliquot (27 ml.) was mixed with a solution of arginine (3.48 g.) in water (30 ml.) and evaporated to dryness under reduced pressure. The residue was triturated with ethanol (50 ml.) to give solid arginine salt of 3-(N-formyl-N-hydroxyamino)propylphosphonic acid (6.76 g.). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonium acetate; hydrogenchloride; triethylsilane; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; acetic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In water; N,N-dimethyl-formamide; acetonitrile; | m/e (ES-) 407.1 (M-H)-. 1.2 Phv-Arg-Ala-Ala-IIb-Ala-Ala-Ala-Papa-NH2 (SEQ ID NO:27) The peptide was constructed by solid phase peptide synthesis (using an automated synthesiser (ABI 430A)) starting with Fmoc-Rink Amide MBHA resin (Novabiochem, 1.587 g, 1 mmol). The coupling and deprotection steps were carried out in the following manner. The Fmoc protecting group was removed by treatment with a 20% solution of piperidine in DMF (two treatments; the first for 3 minutes and the second for 12 minutes; both with 10-20 ml of solution). The resin was washed with DMF (10*10-20 ml). The carboxylic acid (1 mmol) was activated with HBTU (1 equivalent), HOBT (1 equivalent) and DIPEA (2 equivalents) in DMF for approximately 11 minutes before transfer to the resin. The acylation was carried out for approximately 60 minutes and then the resin was washed with DMF (10*10-20 ml). The acylation and washings were repeated (a total of two couplings for each carboxylic acid). This cycle of Fmoc deprotections and couplings was repeated for each of the carboxylic acids. The following acids were used in the following order: The completed resin was collected, washed with methanol and dried for 16 hours in vacuo at 45 C. to give the peptide resin (2.439 g). The peptide was cleaved from the resin and deprotected by treatment with TFA (15 ml), water (2 ml) and triethylsilane (300 mul) for 90 minutes at ambient temperature. The mixture was filtered and the resin was washed with TFA (3*5 ml). The combined filtrate and washings were evaporated and the residue was dissolved in a mixture of water and acetonitrile and freeze-dried. The peptide was partially purified by dividing into 5 portions and carrying out preparative RP-HPLC (Vydac 201 HS1022 column, 250 mm*22 mm) on each portion, loading the crude material in 5 ml of 20% acetonitrile/water with 200 microliters of acetic acid. Elution was carried out using a gradient of acetonitrile-water containing 0.1% TFA (15-45% acetonitrile) over 60 minutes at a flow rate of 12 ml/minute. The fractions containing product were combined and freeze dried to give a white solid (700 mg). The product was then further purified and converted to the acetate salt by preparative RP-HPLC (in 3 portions) eluding with a gradient of buffer A (0.1M ammonium acetate (AR, Fisons) in water) and buffer B (0.1M ammonium acetate in 60% aqueous acetonitrile), using a 35-60% buffer B gradient over 60 minutes at 12 ml/min. Pure fractions were combined and freeze-dried and the freeze-drying was repeated from water until a constant weight was obtained (476 mg). The product was characterised by HPLC, mass spectroscopy and amino acid analysis. RP-HPLC (Vydac C18 column, 201HS, 4.6*250 mm, eluding with acetonitrile and water containing 0.1% TFA, using a 10-40% acetonitrile gradient over 40 minutes, flow rate 1.2 ml/minute) retention time=27.2 minutes. Mass spectroscopy. m/e (ES+) 990.4 (MH+) Amino acid analysis (acid hydrolysis over 24 hours using a solution of 6N HCl containing 1% Phenol at 130 C.) gave Arg 1.16, Ala 4.88, IIb present. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; trifluoroacetic acid; In acetonitrile; | The product was characterised by HPLC, mass spectroscopy and amino acid analysis. RP-HPLC (Vydac C18 column, 218TP54, 4.6*250 mm, eluding with acetonitrile and water containing 0.1% TFA, using a 10-50% acetonitrile gradient over 30 minutes, flow rate 1.0 ml/minute), retention time 18.88 minutes and 19.10 minutes (for the two diastereoisomers). Mass spectrometry, m/e (positive electiospray (ES+)) 1006.7 (MH+). Amino acid analysis (acid hydrolysis over 24 hours using a solution of 6N HCl containing 1% Phenol at 130 C.) gave Arg 1.04, Ala 4.12, Thr 0.85, II present. | |
With hydrogenchloride; | Amino acid analysis (acid hydrolysis over 24 hours using a solution of 6N HCl containing 1% phenol at 130 C.) gave Arg 1.00, Ala 4.12, IIb present, Thr 0.88. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water;Heating / reflux; | Example 8; Preparation of 2-hydro-amino-((E)-methoxy-4-oxobut-2-enoate)-5- guanidinopentanoic acid (arginine monomethylfumarate); <strong>[7200-25-1]Arg</strong>inine (Fluka, 11010, CAS 74-79-3) and MMF (Sigma-Aldrich, 651419, CAS 2756-87-8) in equimolar amounts (0.025 M) were dissolved in 4.0 mL of water. The mixture was stirred and heated until dissolution of all solid material. The solution was transferred to a beaker with 500 mL of acetone, which resulted in formation of a white sticky material. The white sticky material remained after suction filtration and drying in an electrical oven set at 400C. UV- spectrophotometry was used to check the ratio of arginine to MMF (208 nm) in the product. An approximate value for the molar mass was estimated by titration. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 7 Preparation of the Polyamino Acid of Formula (I) in which ; and n=12 (Theoretical Index) This polyamino acid is obtained according to the same procedure as that described in Example 5, but replacing the lysine with the corresponding molar amount of arginine. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With nitric acid; In water; | Compounds/ComponentsA first implementation is an <strong>[7200-25-1]Arg</strong>inine compound of the formula: wherein; R is the <strong>[7200-25-1]Arg</strong>inine group identified and defined above; X is the Amino Acid base identified and defined above; and Y is selected from the group consisting of a Nitrate and a Nitrite. Applicants have cost-effectively synthesized <strong>[7200-25-1]Arg</strong>inine Nitrate by combining nitric acid and <strong>[7200-25-1]Arg</strong>inine, mixing with water, and leaving to crystallize |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With citric acid; In water; at 50℃; for 48h;Product distribution / selectivity; | To about 700 ml of deionized water containing 50 grams citric acid is added 616 grams of arginine to form a clear solution. To this solution of citric acid and arginine is slowly added 55.8 grams of elemental iron. The solution is heated at about 50 C. for 48 hours, or until substantially all the iron is observed to go into solution. The product is cooled, filtered, and dried yielding a ferric trisarginate amino acid chelate. |
Yield | Reaction Conditions | Operation in experiment |
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In ethanol; for 1.5h;Heating / reflux; | Example 5; 1.05 g <strong>[122320-73-4]rosiglitazone</strong> and 426 mg lysine were dissolved in 10 ml boiling methanol (dried) and added to 18 ml ethyl acetate at boiling heat. After about 5 min, the heating bath was removed and the batch was allowed to stand at room temperature overnight. The product was isolated by vacuum filtration, washed with ethyl acetate and dried in the vacuum at 50 C. for 16 h.Yield: 1 g1H spectrum: composition lysine/<strong>[122320-73-4]rosiglitazone</strong> 1:1, about 8% by mole ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; at 20℃; for 37h; | Example 4 2-(2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxamido)-4-guanidinopentanoic acid In a dry round bottomed flask, equipped with a magnetic stirrer, 17.42 g (100 mmol) of <strong>[7200-25-1]Arg</strong>inine is added to 23.43 g (100 mmol) of the oil, N,N'-diisopropyl-O-benzylisourea and stirred at room temperature for about one hour. After about one hour, the volume of the reaction is increased by the addition of 300 mL of dry tetrahyrdofuran (THF), and stirred at room temperature for an additional 36 hours. The resultant mixture is then filtered in order to remove the by-product, diisopropylurea, and the THF is then evaporated from the filtrate at reduced pressure. The oil which remains is pumped under high vacuum for about 24 hours yielding the protected amino acid, benzyl 2-amino-5-guanidinopentanoate, in pure enough form for subsequent steps. A dry, 2-necked round bottomed flask, equipped with a magnetic stirrer and a dropping funnel containing a solution of 10.83 g (52.5 mmol) of N,N'-dicyclohexylcarbodiimide (DCC) dissolved in 60 mL of DCM, is charged with 7.80 g (50 mmol) of orotic acid, 14.54 g (55 mmol) of benzyl 2-amino-5-guanidinopentanoate, and 100 mL of DCM (all of which is under an argon atmosphere). The resultant mixture is stirred in an ice-water bath to cool the solution to a temperature of about 0 C. Following cooling, the solution of DCC from the dropping funnel is added and the reaction is allowed to warm to room temperature and then to stir overnight. The mixture is then filtered through a Celite plug and the filtrate is purified by flash chromatography (ethyl acetate/hexanes; 1/3) to yield the benzyl protected orotate amino acid amide, benzyl 2-(2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxamido)-5-guanidinopentanoate. Lastly, in a single-necked round bottomed flask, 12.06 g (30 mmol) of the benzyl protected orotate amino acid amide is dissolved in 80 mL of a mixture of methanol and tert-butanol (1:1; molar). The catalyst Palladium hydroxide on carbon [Pd(OH)2/C] is added to the mixture, the flask is then sealed with a septum, and purged with hydrogen gas. The reaction is then stirred for 3 hours under a hydrogen atmosphere, and then filtered through Celite. The filtrate is then concentrated in vacuo and then purified by flash chromatography (ethyl acetate/hexanes; 1/5) to yield 2-(2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxamido)-4-guanidinopentanoic acid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To 3 liter three-neck round-bottom flask put with 1568 ml of water, 173 g of arginine is added and dissolved, followed by adjusting the pH of the solution to 9.3 by adding aqueous glycolic acid solution. While being heated at about 60C , the aqueous solution is gradually dropped with 73 g of glycidol over about 1 hour. After the dropping finished, the solution is still left at 60C under agitation for 6 hours to complete reaction. After completion of the reaction, the reaction solution is cooled down to a room temperature and then its pH is adjusted to 6.4 by adding aqueous glycolic acid solution, followed by concentration under a reduced pressure. Thus, glyceryl derivative of arginine containing N-glycerylarginine glycolate as the major component can be obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To 3 liter three-neck round-bottom flask put with 1568 ml of water, 174 g of arginine was added and dissolved, followed by adjusting the pH of the solution to 9.4 by adding 1 N hydrochloric acid. While being heated at about 65C and agitated, the aqueous solution was gradually dropped with 74 g of glycidol over 1 hour. After the dropping finished, the solution was still left at 65C under agitation for 9 hours to complete reaction. After completion of the reaction, the reaction solution was cooled down to a room temperature and then its pH was adjusted to 6.4 by adding 1 N hydrochloric acid, followed by concentration under a reduced pressure to obtain 282g of glyceryl derivative of arginine. Contents of total nitrogen, total carbon and amino nitrogen were measured on the glyceryl derivative of arginine obtained and arginine employed as raw material. The results were as follows.According to the above results, it was confirmed that 80 % ormore of the amino groups in the argininewere reacted with glyceryl group, and it was understood that the maj or component of the obtained glyceryl derivative of arginine was N-glycerylarginine hydrochloride. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water; acetic acid; In ethanol; at 110℃; for 3h; | Example 122 diphenyl(argininate-O,N)borane (880) TG 93, x-Fold 0.98, SOC IC50 7 muM <strong>[7200-25-1]Arg</strong>inine (82 mg) and 2-aminoethyldiphenylborinate (112 mg) were stirred in ethanol (0.4 ml), water (1.5 ml) and acetic acid (0.9 ml) at 110 C. for 3 hr to give the title compound (17 mg). The present compound were also obtained by heating arginine hydrochloride (211 mg) and sodium tetraphenylborate (342 mg) in water (5 mL) at 100 C. for 3 hr. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; dichloromethane; water; for 1h;Reflux; | Example-4: Preparation of Imatinib <strong>[7200-25-1]Arg</strong>inateTo a clear solution of imatinib free base (1 gm, 2.02 mmol) in 4 ml solution of methylene dichloride (3.5 ml) and methanol (0.5 ml), added solution of arginine (0.353 gm, 2.02 mmol) in solution of methanol (2 ml) and water (2 ml) dropwise with continuous stirring and it was refluxed for IH. Added 5 ml acetone and further refluxed the suspension for IH. The suspension was cooled to RT then to 0-5C and stirred for IH. The solid was filtered and washed with 2 ml acetone (0-5C) and dried at 65 C under vacuum (2 mbar) for 4H to give 1.16 gm imatinib arginate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; In water; | The synthesis was performed according to published procedures, as described in (a) Cheng, R. P. W., Y.-J.; Wang, W.-R.; Koyack, M. J.; Suzuki, Y.; Wu, C.-H.; Yang, P.-A.; Hsu, H.-C.; Kuo, H.-T.; Girinath, P.; Fang, C.-J. Amino Acids 2011, in press; (b) Feichtinger, K.; Sings, H. L.; Baker, T. J.; Matthews, K.; Goodman, M. J. Org. Chem. 1998, 63, 8432-8439; (c) Feichtinger, K.; Zapf, C.; Sings, H. L.; Goodman, M. J. Org. Chem. 1998, 63, 3804-3805, which is incorporated herein by reference. 1,4-Dioxane (30 mL) was added to a solution of guanidine hydrochloride (2.8727 g, 30.049 mmol) and sodium hydroxide (4.9573 g, 123.9 mmol) in water (30 mL), the mixture was cooled to 0 C. using an ice water bath. Di-tert-butyl-dicarbonate (14.5296 g, 66.1302 mmol) was then added to the reaction, and the residual was washed into the reaction with another 30 mL of 1,4-dioxane. The reaction was allowed to warm to room temperature and stirred for 3 days. The reaction mixture was then concentrated under reduced pressure to dryness. The resulting white emulsion was diluted with water (60 mL) and extracted with ethyl acetate (3*60 mL). The organic layer was then extracted with 10% citric acid (60 mL), water (60 mL), and brine (60 mL) and dried over anhydrous sodium sulfate. Finally, the dried organic solution was then concentrated under reduced pressure to obtain the desired product as a white powder (5.4 g, 69.2% yield). 1H NMR (400 MHz, CDCl3) 3.46 (s, 1H), 1.46 (s, 18H); ESI-MS calculated for C11H21N3O4 [MH+]=260.3, observed [MH+]=260.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Re-suspend sediment by shaking and 10 minute sonication. Lyophilize suspension to produce un-agglomerated Sirolimus/polyarginine powder solid lyophilisate 66 (Flexi-Dry MP) (step 58). |
Yield | Reaction Conditions | Operation in experiment |
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at 80 - 100℃;Sealed tube; | General procedure: Dimethylformamide dimethyl acetal (Aldrich) with the major component content of 93% was used. Thederivatives of the amino acids (pure grade, 1-3 mg)were prepared via the interaction with 50 muL of DMF dimethyl acetal in sealed glass ampoule with length of 40-50 mm and inner diameter of 2 mm upon heating at 80-100C in the air thermostat of the chromatograph during 1-2 h. The sealing was necessary to prevent losses of volatile DMF dimethyl acetal (bp 102-108C[5]). The reaction course was visually monitored bythe amino acid dissolution. The so prepared mixtures were directly used for the gas chromatography analysis; the chromato-mass spectrometry analysiswas performed using the mixtures diluted with dichloromethane in the 1:500 ratio. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | In ethanol; water; at 50 - 60℃; for 4h; | General procedure: 2-Amino-6-bromobenzothiazole (0.0011 mol) was added to an aqueous alcohol solution of borate 2 (0.001 mol) at 20C. Thereaction mixture was stirred at 50-60C for 4 h. Theprecipitate was filtered off, washed with ethanol, and dried. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Take2.94 g of Tanshinone IIA as a starting material in 100ml of three-neckedflask, then added 10% of Palladium on carbon(Pd/C) about 200mg anddissolved with about 30 ml anhydrous THF, under a hydrogen atmosphere it was Stirred at room temperature for about 1hand the color of the solution was faded. In the reaction flask added Sodiumhydride 500mg ,after stirring the reaction for 2 hours at room temperature thenwas cooled in an ice-water bath thenslowly drop wise added Dibenzyl chlorophosphate 9.5g. After thecompletion of drop wise addition, it was stirred at room temperature for 12h , the reaction was poured into 100 mlof ice water. After standing the organic layer was separated, the aqueous layerwas extracted 1-2 times with an equalvolume of ethyl acetate, combined the organic layers,washed with water, dried using anhydrous Na2SO4, evaporated to dryness to obtain intermediate of dibenzyl phosphoryl tanshinone IIA . This compound wasdissolved in 50ml of anhydrous ethyl acetate , added 5% of Pd/C about 500mg, atroom temperature under a hydrogen atmosphere it was stirred for 12h. thereaction was filtered to remove palladium on carbon, extractred three times byadding an equal amount of water , ethyl acetate layer was discarded, 5. 73g ofarginine was added in the aqueous layer and it was stirred 3 hours at room temperature.Completion of the reaction, the reaction solution was concentrated to about10ml remaining solvent, purificationwith sephadex LH-20 to obtain Tanshinone IIA phenyl phosphate tetra arginine salt desired product(compound 7) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: An aqueous solution of 2-amino-5-guanidinopentanoic acid(arginine) (0.01 mol) in 25 ml water was added to 0.01 mol ofactylacetone in 10ml ethanol and heated at 50 C for 2 h. The metalacetates (0.01 mol) in 20 ml distilled water were added to the reactionmixture of the ligands dropwise and heated under reflux for3 h on a hot plat at 50 C. The mixture was concentrated by evaporation.The precipitated metal complexes (Scheme 1) were filteredoff, washed with water, ethanol, and preserved in a vacuumdesiccator over anhydrous calcium chloride. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: An aqueous solution of 2-amino-5-guanidinopentanoic acid(arginine) (0.01 mol) in 25 ml water was added to 0.01 mol ofactylacetone in 10ml ethanol and heated at 50 C for 2 h. The metalacetates (0.01 mol) in 20 ml distilled water were added to the reactionmixture of the ligands dropwise and heated under reflux for3 h on a hot plat at 50 C. The mixture was concentrated by evaporation.The precipitated metal complexes (Scheme 1) were filteredoff, washed with water, ethanol, and preserved in a vacuumdesiccator over anhydrous calcium chloride. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: An aqueous solution of 2-amino-5-guanidinopentanoic acid(arginine) (0.01 mol) in 25 ml water was added to 0.01 mol ofactylacetone in 10ml ethanol and heated at 50 C for 2 h. The metalacetates (0.01 mol) in 20 ml distilled water were added to the reactionmixture of the ligands dropwise and heated under reflux for3 h on a hot plat at 50 C. The mixture was concentrated by evaporation.The precipitated metal complexes (Scheme 1) were filteredoff, washed with water, ethanol, and preserved in a vacuumdesiccator over anhydrous calcium chloride. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: An aqueous solution of 2-amino-5-guanidinopentanoic acid(arginine) (0.01 mol) in 25 ml water was added to 0.01 mol ofactylacetone in 10ml ethanol and heated at 50 C for 2 h. The metalacetates (0.01 mol) in 20 ml distilled water were added to the reactionmixture of the ligands dropwise and heated under reflux for3 h on a hot plat at 50 C. The mixture was concentrated by evaporation.The precipitated metal complexes (Scheme 1) were filteredoff, washed with water, ethanol, and preserved in a vacuumdesiccator over anhydrous calcium chloride. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; at 20 - 60℃; for 2h; | (0040) D-arginine was prepared in the same manner as in Example 1, with the exception that a D-3-bromocamphor-10-sulfonic acid ammonium salt was used as the optical resolving agent, in lieu of the D-3-bromocamphor-10-sulfonic acid monohydrate, and was used in amounts of 0.9, 1 and 1.1 equivalents (eq.) in Examples 5, 6 and 7, respectively, and the optical purity of the prepared D-arginine was analyzed using a chiral column, as in Example 1. The results are shown in Table 2 below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; at 20 - 60℃; for 2h; | (0026) DL-arginine (42.5 g, 244 mmol) and D-3-bromocamphor-10-sulfonic acid monohydrate (60.3 g, 183 mmol, 0.75 equivalents (eq.)) were added to 1300 mL of methanol, heated to 60 C. so as to be dissolved, and then slowly cooled. (0027) The resulting solution was stirred at room temperature for 2 hr, and the deposited L-arginine and D-3-bromocamphor-10-sulfonic acid salt were filtered off. (0028) Thereafter, the remaining filtrate was concentrated, dissolved in 500 mL of distilled water, passed through a column filled with an ion exchange resin (IRC-86, NH4 type) to adsorb D-arginine, and washed with distilled water. The adsorbed D-arginine was desorbed using 5% ammonia water, and the desorbed aqueous solution was concentrated again, thereby obtaining D-arginine. (0029) The optical purity of D-arginine thus obtained was analyzed using a chiral column (Sumichiral OA-5000 column), and the analysis conditions were as follows. (0030) Column: Sumichiral OA-5000 (5 mum, 4.6±250 mm) (0031) Mobile phase: Solution of 2% acetonitrile dissolved in 2 mM CuSO4 solution (0032) Detector: UV (254 nm) (0033) Based on the results of analysis of the optical purity of D-arginine under the above analysis conditions, D-arginine obtained in an amount of 15.5 g was configured such that D-arginine and L-arginine were present at a ratio of 95:5. (0034) Also, the results of 1H-NMR of the obtained D-arginine were as follows. (0035) 1H-NMR (D2O, 400 MHz): delta 1.43 (m, 4H), 3.02 (m, 2H), 3.09 (m, 1H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With acetic acid; In methanol; at 50℃; | 200 mE of methanol and 80 mE of acetic acid were added with DE-arginine (10 g, 57.4 mmol) and D-3-bromo- camphor-8-sulfonic acid ammonium salt (18.8 g, 57.4 mmol), heated to 500 C. to thus be dissolved, and then slowly cooled. The resulting solution was stirred at 5 C. for 3 hr, and the deposited D-3-bromocamphor-8-sulfonic acid salt of D-arginine was obtained through filtration. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | In water; at 20℃; for 24h; | 8.2 g of <strong>[1405-86-3]glycyrrhizin</strong> and 3.4 g of arginine (1:2) were reacted in a 100 ml aqueous solution at room temperature for 24 hours with vigorous stirring.In the case of 2L of acetone, a large amount of white crystalline powder was precipitated, filtered, and dried under vacuum at 60 C to obtain white crystals.Powder 11.0g, yield 95.0% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In water; acetonitrile; at 45℃; for 0.5h;pH 10; | To a 250 mL round bottom flask, 2 g (4 mmol) of <strong>[27740-01-8]scutellarin</strong> was added, and 10 mL of pure water and 10 mL of acetone were sequentially added.A 4 mol/L aqueous solution of arginine was slowly added dropwise to a pH of 10 under stirring at 45 C, and stirring was continued for about half an hour until the reaction was completed. The reaction solution was filtered through a micropore filter, and about 100 mL of acetone was added to the filtrate, and a large amount of precipitate was precipitated. Stirring was continued for half an hour, followed by suction filtration, and the filter cake was washed with acetone until the filtrate was colorless. The filter cake was collected and dried under reduced pressure at 30 to 40 C to obtain 2.4 g of orange-yellow <strong>[27740-01-8]scutellarin</strong> arginine salt, the yield was 86%, and the chromatographic purity was 99% or more. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88%Spectr. | With hydrogenchloride; sodium hydroxide; potassium hexacyanoferrate(III); In water; water-d2; at 20℃; for 0.333333h;pH 9.5; | General procedure: AA or alpha-amino amide (AA-NH2) (150 mM) was dissolved in degassed H2O/D2O (98:2; 1 ml) and the solution was adjusted to pH 9.5 with HCl/NaOH. Ac-Gly-SH (50 mM) was added and the total volume was adjusted to 2 ml with H2O/D2O (98:2). Potassium hexacyanoferrate(iii) (K3[Fe(CN)6], 150 mM) was added and the solution was stirred at room temperature for 20 min while maintaining the solution at pH 9.5 with NaOH. The resulting suspension was centrifuged and the supernatant was analysed by one- and two-dimensional NMR spectroscopy (1H-1H correlated spectroscopy (COSY), 1H-13C heteronuclear single quantum coherence spectroscopy (HSQC) and 1H-13C HMBC in H2O/D2O (98:2). The yield was quantified using MSM as an internal standard. The ligation product (Ac-Gly-AA-X; X = OH or NH2) was confirmed by 1H-13C HMBC NMR spectral analysis and high-resolution mass spectrometry (HRMS). Reaction mixtures were lyophilized and dissolved in DMSO-d6 or CD3OD for further NMR spectral analysis if 1H-13C HMBC cross-correlation peaks were obscured by the HOD resonance during the original NMR analysis in H2O/D2O (98:2). Yields and HRMS data are given in Table 3, Supplementary Table 8 (Ac-Gly-AA-OH), Extended Data Table 4 and Supplementary Table 9 (Ac-Gly-AA-NH2), and characterization data are provided in Supplementary Information. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.9% | In ethanol; water; at 60℃; for 1h; | Pemetrexed (42.7 g, 0.10 mol) was added to the reaction kettle and 1500 ml of ethanol was added.Heat to 60 C, stir evenly,The solution was incubated at 60 C, and an aqueous solution of arginine (41.8 g, 0.24 mol) was added dropwise to the reaction vessel.Stirring was continued for 1 h, and the temperature was lowered to room temperature.Crystallization 2h, centrifugal filtration, 45 ~ 55 C,Vacuum degree is -0.080~-0.100Mpa vacuum drying for 5-6h, pemetrexed arginine salt,The molar yield is 92.9%.The HPLC purity was 99.60%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With sodium azide; In water; at 40℃; for 2h; | General procedure: Amino acid (10 mmol), sodium azide (0.65 g, 10 mmol) and the Cu nano catalyst (20 mg) were added to a solution of TEOF (4.4 g, 5 mL, 30 mmol) in H2O (5 mL). The solution was stirred and the mixture heated at 40 C for 1-7 h depending on the substrate. Completion of the reaction was monitored by TLC. Then, H2O (20 mL) was added, the Cu catalyst filtered, the filtrate concentrated and the solvent removed in vacuo. The obtained tetrazoles were recrystallized from ethanol and were fully characterized, including satisfactory elemental analyses. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | In N,N-dimethyl acetamide; N,N-dimethyl-formamide; | Place the solid of the common ketone succinic acid monoester obtained in step b in 1 mol of N,N-dimethylformamide and N,N-dimethylacetamide mixed solvent mixed in reflux to dissolve into Changshanone succinic acid monoester,Then, 1.5 mol of arginine was added to the Changshanone succinic acid monoester in batches for stirring and cooled to obtain Changshanone succinic acid monoester arginine salt. |
Tags: 7200-25-1 synthesis path| 7200-25-1 SDS| 7200-25-1 COA| 7200-25-1 purity| 7200-25-1 application| 7200-25-1 NMR| 7200-25-1 COA| 7200-25-1 structure
[ 1119-34-2 ]
(S)-2-Amino-5-guanidinopentanoic acid hydrochloride
Similarity: 0.98
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P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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