Esters-buliding-blocks

Electric Literature of 4934-99-0, These common heterocyclic compound, 4934-99-0, name is Methyl 3-hydroxycyclobutanecarboxylate, 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 solution of methyl 3- hydroxycyclobutanecarboxylate (2 g, 15.37 mmol), 5-methyl-4-nitro-lH-pyrazole (1 .95 g, 15.37 mmol) and PPh3 (6.05 g, 23.06 mmol) in THF (30 mL) was added dropwise DIAD (4.66 g, 23.06 mmol, 4.48 mL) at 0 C and degassed and purged with N2 for 3 times, and then the mixture was stirred at 25 C for 16 h under N2. The reaction mixture was concentrated under reduced pressure to remove THF. The residue was washed with PE:EtOAc (1 : 1, 30 mL), filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (SiO?., PE:EtOAc =: 10: 1 to 5: 1) to give the mixture of trans-methyl 3-(5-methyi-4-nitro-pyrazol-l-yl)cyc3obutanecarboxylate and trans- methyl 3-(3-methy3-4~nitro-pyrazol~l -yl)cyclobutanecarboxylate as a white solid. LCMS: RT 0.729 min, m/z = 240,2 [M + H]+ To a solution of methyl 3-(5-methyi-4-nitro-py razol-l- yl)cyclobutanecarboxylate and methyl 3-(3-methyl-4-nitro-pyrazo3-l~yl)cyclobutanecarboxylate (1.7 g, 7.1 mmol, mixture) in MeOH (20 mL) was added NaBH4 (672 mg, 17.77 mmol) at 0 C. The mixture was stirred at 25 C for 2 h. The reaction mixture was quenched by addition of aq. NH4C1 (20 mL) at 0 C, and extracted with EtOAc (3 * 10 mL), washed with brine (5 mL), dried over Na SCX-i, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (SiO?., PE:EtOAc = 5: 1 to 1 : 1) to give the mixture of trans- [3~(5-methyl-4-nitro~pyrazol-l~yl)cyclobutyl]methanol and fr n.v-[3-(3-methyl-4-nitro-pyrazol-l -yl)cyclobutyl]methanol as a yellow solid. LCMS: RT 0.645 min, m/z == 212.2 [M + H]+.

The synthetic route of 4934-99-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DENALI THERAPEUTICS INC.; ESTRADA, Anthony A.; FENG, Jianwen A.; LYSSIKATOS, Joseph P.; SWEENEY, Zachary K.; DE VICENTE FIDALGO, Javier; (271 pag.)WO2017/87905; (2017); A1;,
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Related Products of 1128-00-3,Some common heterocyclic compound, 1128-00-3, name is Ethyl 2-aminocyclohex-1-enecarboxylate, molecular formula is C9H15NO2, 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 170 mg of ethyl 2-aminocyclohex-1-enecarboxylate as synthesized in Step 7-1-B in 5 ml of pyridine, 70 mg of phosphorus trichloride was added under cooling with ice, followed by 15 minutes’ stirring. Raising the temperature to room temperature, 327 mg of 5-(4-quinoline-2-ylpiperazin-1-yl)hexanoic acid as synthesized in above Step 7-14-C was added to the solution and stirred for 3 hours. Distilling the pyridine off under reduced pressure, the residue was extracted with ethyl acetate and washed with water. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was concentrated under reduced pressure. The residue was purified on silica gel column chromatography (ethyl acetate) to provide 182 mg (38%) of ethyl 2-[5-(4-quinolin-2-ylpiperazin-1-yl)hexanoylamino]cyclohex-1-enecarboxylate. 1H-NMR(CDCl3)delta:11.61(br s,1H),7.86(d,J=8.9Hz,1H), 7.68(d,J=8.5Hz,1H),7.57(d,J=7.7Hz,1H), 7.51(ddd,J=1.2Hz,6.9Hz,8.1Hz,1H),7.22~7.18(m,1H), 6.96(d,J=9.3Hz,1H),4.14(q,J=6.9Hz,2H),3.80~3.70(m,4H), 2.98~2.95(m,2H),2.75~2.65(m,3H),2.64~2.56(m,2H), 2.34(t,J=7.3Hz,2H),2.31~2.28(m,2H),1.81~1.70(m,2H), 1.69~1.56(m,6H),1.26(t,J=6.9Hz,3H),1.01(d,J=6.6Hz,3H) Mass,m/e:478(M+),157(base)

The synthetic route of 1128-00-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASKA Pharmaceutical Co., Ltd.; EP1724267; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

6933-47-7, name is Methyl 4-amino-2-methylbenzoate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 6933-47-7

A solution of 3,5-dichloro-4-ethoxybenzoic acid (1) (285 mg, 1.21 mmol) and DIPEA (1.05 mL, 6.05 mmol) in DMF (2.5 mL) was added to HATU (690 mg, 1.82 mmol) and the orange mixture was stirred for 5 min prior to the addition of methyl 4-amino-2-methylbenzoate (2) (200 mg, 1.21 mmol) in DMF (1 mL). The resulting dark orange solution was stirred overnight for 18 h. 2 M HCl (10 mL) was added and stirring continued for 10 min, and then the mixture was extracted with diethyl ether. The organic layer was washed with water (3*15 mL), dried over MgSO4, filtered and the solvent was evaporated in vacuo. The yellow residue was purified by silica gel chromatography (40 g, 0-100% EtOAc in isohexane) to afford methyl 4-(3,5-dichloro-4-ethoxybenzamido)-2-methylbenzoate (3) (267 mg, 56%): m/z 380 (M-H)- (ES-). 1H NMR (400 MHz, CDCl3) delta: 7.97 (1H, s), 7.80 (3H, m), 7.54 (1H, dd), 7.51 (1H, d), 4.18 (2H, q), 3.89 (3H, s), 2.63 (3H, s), 1.49 (3H, t).

The synthetic route of 6933-47-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KING’S COLLEGE LONDON; US2012/149737; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 685-88-1, name is Diethyl fluoromalonate, 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 685-88-1, COA of Formula: C7H11FO4

Diethyl 2-fluoromalonate (5 g, 28.1 mmol) was added, over 10 min, to a stirred suspension of sodium hydride (1.347 g, 33.7 mmol) in tetrahydrofuran (50 mL) at 0C and the resulting colourless solution was stirred at 0 C for 15 min. and then at RT for 30 min. The solution was cooled to 0 C, a solution of 6-bromohex-l-ene (4.58 g, 28.1 mmol) in THF (20 mL) was then added over 5 min. and the resulting reaction mixture was heated to 60 C and stirred for 16 h. Then the reaction mixture was cooled to 0 C, quenched with ice cold water (100 mL) and extracted with ethyl acetate (2 x 200 mL). The combined organic layer was washed with water (200 mL), brine (200 mL), dried over anhydrous sodium sulphate, filtered and the filtrate concentrated under reduced pressure. The crude product was purified by combiflash chromatography (80 g Redisep S1O2 column, eluting with 10 % EtOAc in n- hexanes) to afford the title compound 162A (5 g, 68%) as a colourless oil. LC-MS retention time = 3.30 min; m/z = 261.2 [M+H]+ KINETIX XB-C18, (75 X 3) mm, 2.6 micron column; Flow rate: 1 mL/min; Mobile Phase A: 10 mM HCO2NH4 in 98% Water/ 2% ACN; Mobile Phase B: 10 mM HCO2NH4 in 2% Water/ 98% ACN; 20% B to 100% B over 4.6 min, then hold 0.4 min. at 20% B with flow rate 1.5 mL/min; Detection: UV at 220 nm. NMR (400MHz, CDCh) delta ppm 5.78 (ddt, J=17.1 , 10.3, 6.6 Hz, 1H), 5.01 (d, J=17.2 Hz, 1H), 4.95 (d, J=6.4 Hz, 1H), 4.34 (q, J=5.6 Hz, 4H), 2.18 – 2.05 (m, 4H), 1.43 – 1.40 (m, 4H), 1.30 (t, J=7.2 Hz, 6H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Diethyl fluoromalonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DEVASTHALE, Pratik; MOORE, Fang; ZHAO, Guohua; PIENIAZEK, Susan Nicole; SELVAKUMAR, Kumaravel; DHANUSU, Suresh; PANDA, Manoranjan; MARCIN, Lawrence R.; (384 pag.)WO2018/89355; (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. 4891-38-7, name is Methyl Phenylpropiolate, A new synthetic method of this compound is introduced below., Safety of Methyl Phenylpropiolate

General procedure: A reaction kettle (30 mL) was charged with aniline (1.0 mmol), and alkyne ester (1.0 mmol). The mixture was stirred at room temperature for 10 minutes, then added terminal alkyne (1.2 mmol, 1.2 eq), AgOTf (5 mol%, 12.9 mg), HOTf (10 mol%, 15 mg), MeOH (2 mL) in the mixture. The mixture was stirred at 120 oC for 24 hours, the mixture was quenched by sat. aq. NaHCO3, and diluted with 20 mL of dichloromethane and washed with 10 mL of H2O. The aqueous layer was extracted twice with dichloromethane (10 mL) and the combined organic phase was dried over Na2SO4. After evaporation of the solvents, the residue was purified by silica gel chromatography (hexane/AcOEt = 5:1) to afford quinoline derivatives. All other compounds are synthesized in a similar manner, with the yields listed in the main text calculated from the isolated, pure products.

The synthetic route of 4891-38-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Yunlan; Zhang, Qiurui; Xu, Xuefeng; Zhang, Xu; Yang, Yurong; Yi, Wei; Tetrahedron Letters; vol. 60; 14; (2019); p. 965 – 970;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics