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CAS No. : | 6915-18-0 | MDL No. : | N/A |
Formula : | C4H4O4 | Boiling Point : | - |
Linear Structure Formula : | HOOCCHCHCOOH | InChI Key : | - |
M.W : | 116.07 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* 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 |
---|---|---|
0.1% - 0.4%Spectr.; 86 - 87%; 0.1% - 0.2%Spectr. | With hydrogenchloride; sodium nitrite; In water; at -15 - 0℃; for 8h; | To a vigorously stirred mixture of mother waters and washing waters (approximately 650 ml) from the previous reaction are added 200 g (1.50 mol) of L-aspartic acid, 360 ml (428.4 g) of 37% HCl (158.51 g of HCl, 4.35 mol) and 100 ml of demineralised water; 184 g (2.66 mol) of solid sodium nitrite are then added in approximately 2 hours at a temperature of ?5 C. under nitrogen blanket. Stirring is continued at the same temperature for 2.5 hours, the temperature is raised to +0 C. in the space of approximately 1 hour, the mixture is left at this temperature for another period of 1 hour, and the temperature then lowered to ?15 C. After 1.5 hours at this temperature, the mixture is vacuum filtered on Buchner filters and left to drain under vacuum pump aspiration for approximately 0.5 hours. The solid is then washed with 80 ml of water at 0 C. and left on a vacuum filter for another 1.5 hours. [00082] The crude product is vacuum dried in an oven at 40 C. It presents approximately 15-20% sodium chloride contamination. [00083] The molar percentages of the impurities present, calculated on the basis of the NMR spectrum, are the following: [TABLE-US-00002] fumaric acid 0.1-0.2% w/w malic acid 0.1-0.4% w/w aspartic acid 0.1-0.2% w/w [00084] The yield of S-(?)-chlorosuccinic acid, calculated 100% pure, is 86-87%. [00085] The pure product, obtained by means of a further crystallisation of a sample of the crude product with water, has a melting point of 180-182 C. [00086] The overall yield of reactions A+B is 83-84%. |
0.1 - 0.4%Spectr.; 80 - 81%; 0.1% - 0.2%Spectr. | With hydrogenchloride; sodium chloride; sodium nitrite; In water; at -15 - 0℃; for 7h; | To a vigorously stirred mixture of 200 g (1.50 mol) of L-aspartic acid, 40 g of sodium chloride (0.68 mol), 440 ml (523.6 g) of 37% HCl (193.74 g of HCl, 5.32 mol), 200 ml of demineralised water, 100 ml of washing waters of the solid obtained in REACTION B (see Example 2), are added 184 g (2.66 mol) of solid sodium nitrite in approximately 2 hours at a temperature of -5 C. under nitrogen blanket. Stirring is continued at the same temperature for 2.5 hours, the temperature is raised to +0 C. in the space of approximately 1 hour, the mixture is left at this temperature for another period of 1 hour and then the temperature is lowered to ?15 C. After 1.5 hours at that temperature, the mixture is vacuum filtered on Buchner filters and left to drain under vacuum pump aspiration for approximately 0.5 hours. The solid is then washed with 80 ml of water at 0 C. and left on a vacuum filter for another 1.5 hours. [00078] The crude product is vacuum dried in an oven at 40 C. It presents approximately 15-20% sodium chloride contamination. [00079] The molar percentages of the impurities present, calculated on the basis of the NMR spectrum, are the following: [TABLE-US-00001] fumaric acid 0.1-0.2% w/w malic acid 0.1-0.4% w/w aspartic acid 0.1-0.2% w/w [00080] The yield of chlorosuccinic acid, calculated 100% pure, is 80-81%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In methanol; diethyl ether; | A solution of 1-(3-pyridyl)-4-tert-butoxycarbonylhomopiperazine (0.91 g, 3.3 mmol), trifluoroacetic acid (7.5 g, 66 mmol) and dichloromethane (30 ml) was stirred for 15 h. The mixture was evaporated. Sodium hydroxide (30 ml, 4 M) was added. The product was extracted two times with dichloromethane (30 ml) and isolated as an oil. Yield 0.50 g, 85%. The corresponding salt was obtained by addition of a diethyl ether and methanol mixture (9:1) saturated with fumaric acid. Mp 172.1-172.9 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | In methanol; diethyl ether; ethyl acetate | 1.A A solution of 1-(3-pyridyl)-piperazine (0.35 g, 2.1 mmol), formic acid (1.0 g, 21.7 mmol), formaldehyde (0.64 g, 37 %) and water (2 ml) was stirred at reflux for 15 h. The mixture was evaporated and sodium hydroxide (30 ml, 1 M) was added and the product was extracted three times with ethyl acetate (15 ml). The corre sponding salt was obtained by addition of a diethyl ether and methanol mixture (9:1) saturated with fumaric acid. Yield 0.21 g, 34 %. Mp 144.5-145.9° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With hydrogen; In ethanol; at 20℃; under 760.051 Torr; for 2.0h; | General procedure: In a typical reaction, 0.015 g of catalyst and 2 mmol of the reactant were taken in 10 mL of ethanol under hydrogen atmosphere. The reaction was monitored by thin-layer chromatography (TLC). After complete disappearance of the starting material, the catalyst was separated by simple filtration and the solvent was removed under reduced pressure to obtain the pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With sodium hydroxide; In ethanol; at 110.0℃; for 72h;pH 7.0;Autoclave; | General procedure: A solution of H2fum (0.2 mmol) or H2glu (0.2 mmol) in 5 mL H2O was adjusted to pH7 with dilute NaOH. Then bix (0.2 mmol) in 5 mL EtOH and CdCl2·2.5H2O (0.2 mmol) in 5 mL H2O were added. The mixture was added to a 30 mL Teflon-lined stainless autoclave and this was sealed and heated to 110C for 3days and then cooled to room temperature to give the colorless crystals 1 in 38% yield based on Cd(II) (0.036 g) or 2 in 46% yield based on Cd(II) (0.035 g). Anal. calcd. for C36H39Cd2Cl2N8O4.50 (1) C, 45.45; H, 4.13; N, 11.78. Found: C, 45.39%; H, 4.08%; N, 11.74%. Anal. calcd. for C26H30Cd2N4O8 (2) C, 41.56; H, 4.02; N, 7.46. Found: C, 41.53%; H, 3.97%; N,7.44 %. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; water; acetone; at 25 - 50℃; for 22h; | 2.4.2. Maleic Acid10294] Compound 1 (246.4 mg, 0.58 mmol, 1 eq.) is suspended in 5% water in acetone (4.95 mE, 20 vols) at 25 C. and the sample is warmed to 50C. Maleic acid (1 M solution in THF) (1.2 mE, 1.22 mmol, 2.1 eq.) is added to the stirred suspension at 50 C. The mixture is cooled to 25 C. at 1 C/mm and stirred at 25 C. for 22 h.10295] The solid was isolated by vacuum filtration and dried under suction.10296] The XRPD analysis confirmed the formation of the formation of a stable non-hygroscopic salt, having an aqueous solubility measured at 0.4 mgmL. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | Stage #1: 2-butenedioic acid With sodium hydroxide In methanol; water at 20℃; Stage #2: 4,4'-dimethyl-2,2'-bipyridines; manganese(II) chloride tetrahydrate In methanol; water at 20℃; for 144h; | A solution of fumaric acid (0.0348 g; 0.3 mmol) in methanol (5 ml) was added to an aqueous solution (5 ml) of sodium hydroxide (0.0240 g; 0.6 mmol), while stirring. Then, a solution of MnCl2*4H2O (0.0593 g; 0.3 mmol) in deionized water (5 ml) was added, under constant stirring. Finally, a solution of 4,4'-dimethyl-2,2'-bipyridine (0.0552 g; 0.3 mmol) in methanol (5 ml) was added. A translucent yellow solution was obtained. After six days, the yellow crystals so obtained were filtered out, washed with a 50:50 deionized water-methanol mixture and air dried. Yield: 42 % based on metal precursor. Anal. calc.for C32H34Mn2N4O11 (FW = 724.48): C, 53.05; H, 4.17; N, 7.73 %. Found: C, 52.86; H, 4.29; N, 7.68 %. IR(cm-1): 3630 (s), 3500 (s, br), 3080 (m), 3060(s), 2960 (m), 2920 (m), 1960 (m), 1940 (m), 1880 (w), 1820 (w), 1600(vs), 1550 (vs), 1480 (s), 1390 (s), 1300 (m), 1240 (m), 1210 (m), 1130 (w), 1010 (s), 980 (m), 918 (s), 833 (s), 802(s), 706 (m), 690 (vs, sh), 660 (s), 586 (s), 548 (m), 513(m), 424 (w). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: phenergan; 2-butenedioic acid In acetonitrile for 1.5h; Milling; Stage #2: In acetonitrile at 4.84℃; for 48h; | 2.1.2. Preparation of PTZ-Cl-fumaric Promethazine hydrochloride (150 mg) was mixed with fumaric acid (27.2 mg)in a 2:1 molar ratio. The powder was mechanically activated ina ball mill for 90 min at 27 Hz after the addition of a few drops of acetonitrile. In order to obtain single crystals, the powderobtained in the mill was recrystallized from acetonitrile (4 ml).The solution obtained was kept at 278 K for 48 h and afterwardsat room temperature, allowing for slow evaporation ofthe solvent and for crystals suitable for single-crystal X-raystructure analysis to be obtained. | |
In acetonitrile at 4.84℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28.7 g | With dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 4h; | Add 35.6g (0.2mol) compound 1 in the reaction flask11.6g (0.1mol) compound 2, 500ml dichloromethane stirred,Add 51.7g (0.25mol) DCC at room temperature, then stir at room temperature for 4 hours,Check that the raw materials disappeared; add water and stir to separate the layers. The aqueous layer was extracted twice with dichloromethane and the dichloromethane layers were combined, washed with water, dried over anhydrous sodium sulfate, spin-dried to dry the solvent, dissolved in toluene, and then chromatographed on a silica gel column. It was recrystallized twice with toluene and ethanol to obtain the target compound, 28.7 g of white solid, HPLC: 99.2%. The resulting NMR spectrum of the compound represented by formula I is shown in FIG. 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72.75% | In methanol; toluene at 25 - 35℃; | 1-3 Preparation of compound 6 Between 25 and 35°C, add 750 g of the methanol solution of compound 6 fumaric acid to the toluene solution of compound 4 obtained in the previous step. During the dropwise addition, white solids are precipitated in the system. , the filter cake was dried at 50°C to obtain a white solid; Add 1kg of purified water and 1kg of methanol to the white solid obtained in the previous step, heat up to 65-70°C, stir to dissolve, keep stirring at 0-10°C for crystallization for 1-2h, and filter. The filter cake was rinsed once with methanol-water mixture, and the filter cake was dried at 45° C. to obtain 203.15 g of white solid compound 7, vonolaxan fumarate, with a purity of 100%, mono-hetero |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With tetrabutylammonium decatungstate In lithium hydroxide monohydrate; acetonitrile at 30℃; Inert atmosphere; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | In ethanol at 20℃; for 0.5h; | 5 Example 5: Preparation of (2R,3R,4R,5R)-2-(4-amino-5-deuterated pyrrolo[2,1-f][1,2,4]triazin-7-yl)- 2-cyano-5-(isobutyryloxymethyl)tetrahydrofuran-3,4-diylbis(2-methylpropionate)maleate Compound Z (2.85 g, 5.67 mmol) was dissolved in absolute ethanol (20 mL), maleic acid (0.66 g, 5.67 mmol) was added, heated to reflux, and the reaction solution was cooled to room temperature after 30 minutes, and n-heptane ( 40mL), a large amount of cotton wool-like solid was precipitated, the temperature was raised to 45°C, stirred for 1.5 hours, then cooled to 0°C, continued to stir for 30 minutes, filtered, and the filtrate was dried to obtain the title compound in the form of a white solid (2.5g, yield 71 %, HPLC purity 98.9%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10 g | In chloroform at 20℃; | 13 Example 13 preparation of relugo limaleate The crude relugoli (12.5g) prepared in Example 2 was sequentially added with chloroform (0.12L) and maleic acid (3.48g, 0.03mol, 1.5eq.) at room temperature, after feeding, stirring for 3 hours, solids precipitated, continued stirring for 12 hours, filtered, and the filter cake was washed withCHCl 3(50mL). The wet product is vacuum dried to obtain relugo limaleate (white solid; 10.0g HPLC purity: 98.99%) |
Tags: 6915-18-0; But-2-enedioic acid;
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