Category: 33993-24-7

Reference of 33993-24-7,Some common heterocyclic compound, 33993-24-7, name is Cyclopropanecarboxylic anhydride, molecular formula is C8H10O3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A mixture of 20 g (136 mmol) 1 ,3,5-triazine-2,4-diamine hydrochloride (GAS-No of free base:504-08-5), 500 mL water and 20 g (130 mmol) cyclopropanecarbonyl cyclopropanecarboxylate was stirred for 1 day at RT. 20 g (130 mmol) cyclopropanecarbonylcyclopropanecarboxylate was added into the reaction and stirring was continued for 1 day at room temperature. Another batch of 20 g (130 mmol) cyclopropanecarbonyl cyclopropanecarboxylate was added and stirring was continued for 3 days at room temperature. The above procedure was repeated once and the solutions of two batch reaction were combined. The solids were filtered off and the crude product purified by FlashPrep-HPLC (column: 018 silica gel; mobile phase, ACN/water (0.05% NH4OH) =5% increasing to ACN/water (0.05% NH4OH)=20% within 12 mm; Detector, UV 254 nm) to give10.5 g (22%) of the title compound.LC-MS: m/z = 180 [M÷H].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Cyclopropanecarboxylic anhydride, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BAYER AKTIENGESELLSCHAFT; KLAR, Ulrich; BOHLMANN, Rolf; SCHAeCKE, Heike; SUeLZLE, Detlev; MENZ, Stephan; PANKNIN, Olaf; (249 pag.)WO2018/134148; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 33993-24-7, name is Cyclopropanecarboxylic anhydride, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 33993-24-7, Computed Properties of C8H10O3

[0410] A solution of 315D (50.6 mg, 0.19 mmol) and cyclopropanecarboxylic acid anhydride (302 mg, 1.96 mmol) in dioxane (2 mL) was heated to 93 C. overnight. The mixture was concentrated in vacuo, diluted with EtOAc and washed with satd. Aq. KHCO3 solution (2×). The organic extract was dried (Na2SO4), filtered and concentrated. The residue was triturated with ether to obtain the title compound (11 mg, 17%) as a white solid.

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Reference:
Patent; Das, Jagabandhu; Padmanabha, Ramesh; Chen, Ping; Norris, Derek J.; Doweyko, Arthur M.P.; Barrish, Joel C.; Wityak, John; Lombardo, Louis J.; Lee, Francis Y.F.; US2004/54186; (2004); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 33993-24-7, name is Cyclopropanecarboxylic anhydride, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 33993-24-7

Step 1 : To a solution of methyl 2-isocyanoacetate (72.7 g, 729 mmol) and DBU (1 1 1 g, 729 mmol) in THF (1 L) was added a solution of cyclopropanecarboxylic anhydride (112 g, 729 mmol) in THF (100 mL) portionwise at 5C. The mixture was stirred at rt overnight, concentrated and purified by flash chromatography (PE/EtOAc = 5:1 ) to afford methyl 5-cyclopropyloxazole-4- carboxylate lnt-1 a-11. 1H-NMR (CDCI3, 300 MHz): delta 1.04-1.18 (m, 4H), 2.74-2.79 (m, 1 H), 3.91 (s, 3H), 7.60 (s, 1 H)

According to the analysis of related databases, 33993-24-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GILEAD SCIENCES, INC.; KINZEL, Olaf; KREMOSER, Claus; SCHMITT, Aaron C.; GEGE, Christian; (205 pag.)WO2016/96115; (2016); A1;,
Ester – Wikipedia,
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Synthetic Route of 33993-24-7, A common heterocyclic compound, 33993-24-7, name is Cyclopropanecarboxylic anhydride, molecular formula is C8H10O3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a suspension of Compound Int-28d (0.51 g, 1.87 mmol) in CH2CI2 (3 mL) was added cyclopropyl anhydride (2 mL). The resulting reaction was allowed to stir at room temperature for 2 hours, then a solution of 4M HCl in dioxane ( 3 mL) was added and the reaction was allowed to stir at room temperature for 2 hours. The reaction mixture was then filtered and the collected solid was washed with hexane and dried in vacuo to provide Compound Int-29a (590 mg). MS (ESI) m / e (M+H+): 323.

The synthetic route of 33993-24-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KOZLOWSKI, Joseph A.; ROSENBLUM, Stuart B.; COBURN, Craig A.; SHANKAR, Bandarpalle, B.; ANILKUMAR, G., Nair; CHEN, Lei; DWYER, Michael, P.; JIANG, Yueheng; KEERTIKAR, Kartik, M.; LAVEY, Brian, J.; SELYUTIN, Oleg, B.; TONG, Ling; WONG, Michael; YANG, De-Yi; YU, Wensheng; ZHOU, Guowei; WU, Hao; HU, Bin; ZHONG, Bin; SUN, Fei; JI, Tao; SHEN, Changmao; RIZVI, Razia; ZENG, Qingbei; WO2012/41014; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 33993-24-7, name is Cyclopropanecarboxylic anhydride, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H10O3

Example 3 3,6,14-Tris(cyclopropylcarboxy)oxymorphone A suspension of oxymorphone (1.56 g; 5.19 mmol), cyclopropylcarboxylic acid anhydride (4.0 g; 25.95 mmol), and toluene (20 mL) was stirred at 80 C. for 160 min. Then DABCO was added in one portion (1.16 g; 10.38 mmol) and the resulting mixture was stirred at 80 C. over 15 h. After this time the conversion was incomplete and an additional amount of anhydride (1.60 g; 10.38 mmol) was added and mixture was stirred at 80 C. for 5 h. Then the reaction mixture was allowed to cool down, concentrated in vacuo, and the excess anhydride was removed under high vacuum. The mixture was diluted with dichloromethane (20 mL), washed with sat. NaHCO3 (5 mL) and the aqueous layer was extracted with dichloromethane (3*5 mL). Combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated. Column chromatography (eluent EtOAc?EtOAc+10% MeOH) afforded 2.37 g (90%) of the title compound as a white solid. This reaction could also be performed using cyclopropylcarboxylic acid chloride (less expensive) and triethylamine in ethyl acetate as the solvent at 80 C. to obtain 92% of the titled compound. mp 158-160 C. (EtOH); Rf 0.40 (ethyl acetate:hexane/1:1); [alpha]22D=-122.96 (c=1.0, CHCl3); IR(CHCl3) v 3025, 2934, 2849, 1743, 1716, 1440, 1387, 1100, 1032 cm-1; 1H NMR (600 MHz, CDCl3) delta 6.86 (d, J=8.2 Hz, 1H), 6.67 (d, J=8.2 Hz, 1H), 5.42 (dd, J=6.0, 1.6 Hz, 1H), 5.08 (s, 1H), 4.22 (d, J=6.0 Hz, 1H), 3.21 (d, J=18.8 Hz, 1H), 3.05 (dd, J=18.3, 6.2 Hz, 1H), 2.55 (dd, J=18.8, 6.2 Hz, 1H), 2.47 (dd, J=11.8, 4.7 Hz, 1H), 2.38 (ddd, J=12.3, 12.3, 5.2 Hz, 1H), 2.31 (s, 3H), 2.22 (ddd, J=12.0, 12.0, 3.4 Hz, 1H), 2.04 (d, J=18.4 Hz, 1H), 1.87 (m, 1H), 1.77-1.69 (m, 1H), 1.65-1.58 (m, 2H), 1.21 (m, 1H), 1.18 (m, 1H), 1.14-1.09 (m, 3H), 1.05 (m, 1H), 1.04-1.00 (m, 2H), 0.99-0.94 (m, 2H), 0.90-0.82 (m, 2H); 13C NMR (150 MHz, CDCl3) delta 174.08, 173.21, 172.47, 147.37, 143.85, 133.30, 131.59, 130.69, 122.69, 118.87, 116.56, 86.88, 81.02, 57.45, 47.06, 45.07, 42.87, 30.28, 27.27, 22.96, 14.52, 12.97, 12.81, 9.367, 9.23, 9.16, 9.05, 8.55, 8.43; MS (+EI) m/z (%): 41 (48), 56 (55), 69 (100), 86 (100), 124 (20), 167 (16), 437 (16), 505 (12); HRMS calcd for C29H31NO7 505.2101. found 505.21049.

According to the analysis of related databases, 33993-24-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Brock University; US2012/283444; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 33993-24-7, name is Cyclopropanecarboxylic anhydride, molecular formula is C8H10O3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Recommanded Product: 33993-24-7

Example 1; General Procedure for Demethylation/Acylation; Tertiary amine (0.1 mmol, 1.0 eq.) was dissolved in acetic anhydride (1 ml) and Pd(OAc)2 (0.01 mmol, 0.1 eq.) added. The reaction was heated at 80 C. for 15 hours, cooled to room temperature and passed through a plug of silica using CHCl3:MeOH:NH4OH 80:20:1 as eluent. The volatiles were removed in-vacuo, and the residue suspended in NaHCO3. The aqueous phase was extracted with CHCl3, and the combined organic extracts washed with 1M HCl and brine before being dried over magnesium sulphate, filtered and the volatiles removed in-vacuo to yield the acyl product.It will be understood by a person skilled in the art that the above description for Example 1 is provided for the general procedure. The examples shown below in Examples 1a-1j follow the general procedure outlined above, and shown in Scheme I from compound 3 to 7, but include the use of different sources of palladium and different amounts of Pd(OAc)2, where applicable, and the use of different solvents, as indicated in the table below.; Example 2; Reactivity of a Series of Anhydrides; The reactivity of a series of anhydrides was explored following the general procedure outlined in Example 1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 33993-24-7, its application will become more common.

Reference:
Patent; Brock University; US2009/5565; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 33993-24-7,Some common heterocyclic compound, 33993-24-7, name is Cyclopropanecarboxylic anhydride, molecular formula is C8H10O3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A mixture of 20 g (136 mmol) 1 ,3,5-triazine-2,4-diamine hydrochloride (GAS-No of free base:504-08-5), 500 mL water and 20 g (130 mmol) cyclopropanecarbonyl cyclopropanecarboxylate was stirred for 1 day at RT. 20 g (130 mmol) cyclopropanecarbonylcyclopropanecarboxylate was added into the reaction and stirring was continued for 1 day at room temperature. Another batch of 20 g (130 mmol) cyclopropanecarbonyl cyclopropanecarboxylate was added and stirring was continued for 3 days at room temperature. The above procedure was repeated once and the solutions of two batch reaction were combined. The solids were filtered off and the crude product purified by FlashPrep-HPLC (column: 018 silica gel; mobile phase, ACN/water (0.05% NH4OH) =5% increasing to ACN/water (0.05% NH4OH)=20% within 12 mm; Detector, UV 254 nm) to give10.5 g (22%) of the title compound.LC-MS: m/z = 180 [M÷H].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Cyclopropanecarboxylic anhydride, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BAYER AKTIENGESELLSCHAFT; KLAR, Ulrich; BOHLMANN, Rolf; SCHAeCKE, Heike; SUeLZLE, Detlev; MENZ, Stephan; PANKNIN, Olaf; (249 pag.)WO2018/134148; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 33993-24-7, name is Cyclopropanecarboxylic anhydride, A new synthetic method of this compound is introduced below., Safety of Cyclopropanecarboxylic anhydride

Example 9 (diastereomeric mixture)To a solution of example 9a (0.055 g, 0.12 mmol) in dry ACN (2 mL), dicyclopropyl anhydride (0.075 g, 90% content, 0.44 mmol, prepared as described in J. Org. Chem., 67, 5226-5231; 2002) and dry TEA (0.088 mL, 0.62 mmol) are added and the mixture heated under microwaves irradation (100C) for 50 min and then heated at 150C for additional 30 min. Solvents evaporated, crude purified by flash cromatography (cycloheane/EtOAc from 50:50 to 20:80) to obtain the title compound (0.033 g, 54%).HPLC-MS (Method 6): Rt = 10.80 minMS (ESI pos): m/z = 486 (M+H)+ The diastereoisomers of the title compound are separated by HPLC using a chiral stationary phase.Method for separation:HPLC apparatus type: Agilent 1100; column: Daicel chiralpack AS-H, 5.0 muiotaeta, 250 mm x 20 mm; method: eluent hexane/EtOH 70:30; flow rate: 15 mL/min, Temperature: 25C; UV Detection: 230 nm Example of separation by chiral HPLC:Sumitted to separation: 200 mg of Example 9Obtained: 84 mg of Diastereoisomer 1 (Exp. 10) and 78 mg of Diastereoisomer 2 (Exp.11)Example Chiral HPLC HPLC-MS (Method 5): MS (APCI pos):Rt [min] Rt [min] m/z

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GIOVANNINI, Riccardo; BERTANI, Barbara; FERRARA, Marco; LINGARD, Iain; MAZZAFERRO, Rocco; ROSENBROCK, Holger; WO2013/17657; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

A common heterocyclic compound, 33993-24-7, name is Cyclopropanecarboxylic anhydride, molecular formula is C8H10O3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 33993-24-7.

General procedure: To a stirred solution of 7 (107 mg, 0.20 mmol), TEA (82 muL,0.60 mmol) and DMAP (10 mg, 0.08 mmol) in dry DCM (10mL) acetic anhydride (57 muL, 0.60 mmol) was added dropwiseat 0 C. Then, the reaction mixture was allowed to stir at roomtemperature overnight. The mixture was concentrated anddiluted with H2O (20 mL) and extracted with EtOAc (2¡Á10mL). The combined organic layers were washed with H2O(2¡Á20 mL), brine (20 mL), and dried over Na2SO4. The mixturewas cooled to room temperature, slowly diluted with H2O(100 mL) and extracted with EtOAc (2¡Á100 mL). The combinedorganic layers were washed with H2O (2¡Á150 mL), brine(150 mL), dried over Na2SO4 and concentrated. The residuewas purified by flash chromatography using 5% EtOAc inpetroleum ether to yield 77 mg (0.13 mmol, 65%) of product asa white pure solid.

The synthetic route of Cyclopropanecarboxylic anhydride has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Xiao-Yin; Zhang, Shu-Yong; Li, Jing; Liu, Hua-Nan; Xie, Xin; Nan, Fa-Jun; Acta Pharmacologica Sinica; vol. 35; 11; (2014); p. 1463 – 1472;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

33993-24-7, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 33993-24-7, name is Cyclopropanecarboxylic anhydride belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Will contain water (0.32 ml) with trifluoroacetic acid (4.2 ml) cooled to -5 C the solution, and ethyl-N-[(mesitylsulfonyl)oxy]ethaneimidate (2.29 g, 8.02 mmol) blending and the stirring the mixture at room temperature for up to 1 hour. The reaction mixture with ice-water (20 ml) then mixes and with dichloromethane (20 ml) extraction. The sodium sulfate machine in on the drying and filtering, and the obtained solution for the 0 C dropwise to 5-bromo-4-methylpyridin-2-amine (1 g, 1.79 mmol) in dichloromethane (15 ml) in solution. The mixture stirred at room temperature for 1 hour and then with diethyl ether (20 ml) incorporation. The precipitated solid is filtered out of the diethyl ether is used for cleaning. The solid for drying under high vacuum. This produced 1.22 g (theoretical value of 57%) of the 1,2-diamino-5-bromo-4-methylpyridinium-2,4,6-trimethylbenzolsulfonate. The 1,2-diamino-5-bromo-4-methylpyridinium-2,4,6-trimethylbenzolsulfonate (580 mg, 1.44 mmol) and cyclopropylcarboxylic acid anhydride (1.33 g, 8.65 mmol) in pyridine (2.5 ml) in solution in 100 C stirring up to 8 hours. The reaction mixture is concentrated in the rotary evaporator and the residual substance is dissolved in DMSO/water/b in nitrile. By this solution the sealing ripoll filter filtering and by preparative HPLC (eluents: acetonitrile/water with 0.1% trifluoro acetic acid the gradient) to be purified. This generating 279 mg (theoretical value of 69%) the subject compound.

The synthetic route of 33993-24-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ROEHN, ULRIKE; ELLERMANN, MANUEL; STRASSBURGER, JULIA; WENDT, ASTRID; ROEHRIG, SUSANNE; WEBSTER, ROBERTALAN; SCHMIDT, MARTINAVICTORIA; TERSTEEGEN, ADRIAN; BEYER, KRISTIN; SCHAEFER, MARTINA; BUCHMUELLER, ANJA; GERDES, CHRISTOPH; SPERZEL, MICHAEL; SANDMANN, STEFFEN; HEITMEIER, STEFAN; HILLISCH, ALEXANDER; ACKERSTAFF, JENS; TERJUNG, CARSTEN; (148 pag.)TW2016/5809; (2016); A;,
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Ester – an overview | ScienceDirect Topics