Category: 33689-29-1

Electric Literature of 33689-29-1,Some common heterocyclic compound, 33689-29-1, name is Methyl 1-hydroxycyclopropanecarboxylate, molecular formula is C5H8O3, 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 solution of methyl 1-hydroxycyclopropanecarboxylate (0.741 mL, 8.61 mmol) was added diisopropylcarbamic chloride (1.550 g, 9.47 mmol) and DIEA (2.256 mL, 12.92 mmol) in DCM (15 mL). The resulting solution was stirred at rt for 2 h, then diluted with DCM and the organic layer was washed with 1 N HC1,water and brine, dried (Mg504), filtered and concentrated. The residue was purified via Biotage (15% to 30% EtOAc/Hex; 25 g column) to yield Cap L-9 Step a (0.66 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 1-hydroxycyclopropanecarboxylate, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HEWAWASAM, Piyasena; LOPEZ, Omar D.; TU, Yong; WANG, Alan Xiangdong; XU, Ningning; KADOW, John F.; MEANWELL, Nicholas A.; GUPTA, Samayamunthula Venkata Satya Arun Kumar; KUMAR, Indasi J. Gopi; PUNUGUPATI, Suresh Kumar; BELEMA, Makonen; WO2015/5901; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 33689-29-1, name is Methyl 1-hydroxycyclopropanecarboxylate, 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 33689-29-1, Recommanded Product: 33689-29-1

To a solution of methyl l-hydroxycyclopropanecarboxylate (1.0 g, 8.62 mmol) and 3,4-dihydropyrane (0.86 mL, 9.42 mmol) in dichloromethane (20 mL) was added pyridinium-/ -tolucnc sulfonic acid (216 mg, 0.86 mmol) at RT. The mixture was stirred overnight at RT. The solvent was removed under vacuum and the residue was purified by flash column chromatography to yield 990 mg of the desired product. NMR (400 MHz, CDCb) d 1.30-1.32 (m, 2H), 1.54-1.58 (m, 6H), 1.82-1.85 (m, 2H), 3.47-3.53 (m, 1H), 3.74 (s, 3H), 3.83-3.89 (s, 1H), 4.89-4.91 (m, 1H).

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Reference:
Patent; ICHNOS SCIENCES S.A.; CHAUDHARI, Sachin, Sundarlal; GHARAT, Laxmikant, Atmaram; IYER, Pravin; DHONE, Sachin, Vasantrao; ADIK, Bharat, Gangadhar; WADEKAR, Prashant, Dilip; GOWDA, Nagaraj; BAJPAI, Malini; (233 pag.)WO2020/70331; (2020); 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. 33689-29-1, name is Methyl 1-hydroxycyclopropanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 33689-29-1

Piperidine-1-carbonyl chloride (1.599 mL) was added to a solution of methyl 1-hydroxycyclopropanecarboxylate (1 mL) and DIEA (3.04 mL) in DCM (15 mL). The resulting solution was stirred at rt for 2 h, then diluted with DCM and the organic layer was wahed with iN HC1, water and brine, dried (Mg504), filtered andconcentrated. The residue was purified with silica gel gel to yield Cap L-7 Step a (0.75 g).

According to the analysis of related databases, 33689-29-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HEWAWASAM, Piyasena; LOPEZ, Omar D.; TU, Yong; WANG, Alan Xiangdong; XU, Ningning; KADOW, John F.; MEANWELL, Nicholas A.; GUPTA, Samayamunthula Venkata Satya Arun Kumar; KUMAR, Indasi J. Gopi; PUNUGUPATI, Suresh Kumar; BELEMA, Makonen; WO2015/5901; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 33689-29-1,Some common heterocyclic compound, 33689-29-1, name is Methyl 1-hydroxycyclopropanecarboxylate, molecular formula is C5H8O3, 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.

Compound 1-8A mixture of Inter mediate-2 (15 mg, 1 equiv.) and methyl 1-hydroxycyclopropanecarboxylate (14 mg, 3 equiv.) in THF was cooled to -78 C. Contents were treate with sodium hydride (5.3 mg, 60% suspension in mineral oil, 3 equiv.) and warmed to 23 C and stirred for 18 h. The contents were concentrated in vacuo, and the residue was purified via silica gel chromatography utilizing a 0-30% ethyl acetate/hexanes gradient to deliver the desired compound (16 mg, 84%>) as a white solid. 1H-NMR (500 MHz, CDCb) delta 8.47 (s, 2 H), 7.23-7.17 (m, 1 H), 7.16 (s, 1 H), 7.02 (t, 1 H), 6.98 (t, 1 H), 6.93-6.88 (m, 1 H), 6.58 (s, 1 H), 5.95 (s, 2 H), 3.70 (s, 3 H), 1.76-1.71 (m, 2 H), 1.45-1.40 (m, 2 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 1-hydroxycyclopropanecarboxylate, its application will become more common.

Reference:
Patent; IRONWOOD PHARMACEUTICALS, INC.; RENNIE, Glen Robert; PERL, Nicholas; LEE, Thomas Wai-Ho; RENHOWE, Paul Allan; NAKAI, Takashi; MERMERIAN, Ara; IM, G-Yoon Jamie; (235 pag.)WO2016/44445; (2016); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 33689-29-1, These common heterocyclic compound, 33689-29-1, name is Methyl 1-hydroxycyclopropanecarboxylate, 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 stirred 0 C solution of methyl l -hydroxyeyclopropane-I- carboxylate (1 16 mg, 1.00 mmol, 1.00 equiv) in DMF (4 mL) was added sodium hydride (60 mg, 1.50 mmol, 1.50 equiv, 60% in mineral oil) in several batches. The resulting reaction mixture was stirred for 0.5 h at 0 C, then 2-(bromomethyl)-l,4- dichlorobenzene (238 mg, 0.99 mmol, 0.99 equiv) was added. The resulting reaction mixture was stirred for 1 h at room temperature and quenched by the addition of water (20 mL). The resulting solution was extracted with ethyl acetate (3×20 mL) and the combined organic layers washed with, brine (20 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to provide 270 mg (98%) of 85a as a yellow oil.

The synthetic route of 33689-29-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARDELYX, INC.; LEWIS, Jason, G.; REICH, Nicholas; CHEN, Tao; JACOBS, Jeffrey W.; CHARMOT, Dominique; NAVRE, Marc; FINN, Patricia; CARRERAS, Christopher; SPENCER, Andrew; WO2013/96771; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 33689-29-1,Some common heterocyclic compound, 33689-29-1, name is Methyl 1-hydroxycyclopropanecarboxylate, molecular formula is C5H8O3, 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.

Copper (I) iodide (650 mg, 3.41 mmol) and triethylamine (3.0 mL, 22 mmol) were added to a stirred solution of methyl 1-hydroxycyclopropanecarboxylate (2.0 g, 17.22 mmol) in acetonitrile (60 mL) at rt in a sealed tube. The reaction mixture was heated to 50 C and 2-fluorosulfonyl-2,2- difluoroacetic acid (15.0 g, 84.23 mmol) was added and stirred at 50 C at 18 h, then concentrated under reduced pressure at 30 C bath temperature. To the residue water (100 mL) was added and extracted with EtOAc (2 x 150 mL). The combined organic layers were washed with brine, dried (Na2S04), filtered and concentrated under reduced pressure at 30 C bath temperature which gave the title compound (1.1 g) as liquid. The compound was used in next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 1-hydroxycyclopropanecarboxylate, its application will become more common.

Reference:
Patent; MEDIVIR AKTIEBOLAG; ERSMARK, Karolina; KARLSTROeM, Sofia; KLASSON, Bjoern; LUNDGREN, Stina; ROSENQUIST, Asa; SALVADOR ODEN, Lourdes; (155 pag.)WO2018/226150; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 33689-29-1, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 33689-29-1 as follows.

Example B6 A 0 C. solution of methyl 1-hydroxycyclopropane-1-carboxylate (1 g, 8.61 mmol) in DMF (10 mL) was treated with NaH (60% in mineral oil, 0.689 g, 17.22 mmol), stirred at 0 C. for 0.5 h, treated with iodomethane (0.646 mL, 10.33 mmol), allowed to slowly warm to RT and stirred for 2 h. The mixture was quenched with satd. NH4Cl, diluted with water and extracted with Et2O (3*). The combined organics were washed with water, then brine, dried and concentrated to afford methyl 1-methoxycyclopropane-1-carboxylate (1.10 g, 98%). 1H NMR (400 MHz, DMSO-d6): delta 3.62 (s, 3H), 3.27 (s, 3H), 1.12-1.11 (m, 4H).

According to the analysis of related databases, 33689-29-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Caldwell, Timothy Malcolm; Samarakoon, Thiwanka; Vogeti, Lakshminarayana; Kaufman, Michael D.; Patt, William C.; Ahn, YuMi; US2014/275016; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 33689-29-1, 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. 33689-29-1, name is Methyl 1-hydroxycyclopropanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Step 1 : methyl 1-(5-bromo-4-fluoro-2-nitrophenoxy)cvclopropanecarboxylate: To a mixture of methyl 1-hydroxycyclopropanecarboxylate (Aldrich) (1.0 g, 8.8 mmol) and 15- crown-5 (cat. amount) in THF (30 ml) was added NaH (400 mg, 10 mmol) at room temperature. The resulting mixture was stirred at room temperature for 30 min and then added 1-bromo-2,5- difluoro-4-nitrobenzene (Aldrich) (2 g, 8.4 mmol). The mixture was stirred at room temperature for additional 16 hrs. When TLC indicated the reaction was completed, the reaction mixture was quenched with saturated NH4CI aqueous solution. After removal of the organic solvent, the mixture was extracted with ethyl acetate (x3). The combined organic phases were washed with brine (x3), dried over anhydrous Magnesium sulfate and filtered. The filtration was concentrated under reduced pressure to give the crude product, which was purified by flash column chromatography on silica gel using a gradient 0-10% ethyl acetate in hexanes to afford the title compound as yellow solid. LC-MS: Rt=1.43 mins; MS m/z [M+H]+ 333.9; Method 5-95AB 1.5minLC_v003 1H NMR (400 MHz, CDCI3) delta 8.15 (1 H, d), 6.98 (1 H, d), 3.57 (3H, s), 1.38 (2H, m), 1.18 (2H, m).

The chemical industry reduces the impact on the environment during synthesis Methyl 1-hydroxycyclopropanecarboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS AG; CHEN, Shuhui; HE, Haiying; LAGU, Bharat; QIN, Hua; WU, Chengde; XIAO, Yisong; WO2015/102929; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics