Esters-buliding-blocks

581065-95-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 581065-95-4 name is tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

BOP (0.3 g, 0.73 mmol) and DIPEA (0.26 mL, 1.52 mmol) were added to a suspension of 11 (0.1 g, 0.15 mmol) and amino-CH2CH2-POE4-CO2tBu (0.21 g, 0.67 mmol) in DMF (6 mL). The reaction mixture was stirred for 96 hours at room temperature, and the solvent was evaporated under reduced pressure. The residue was dissolved in CH2Cl2, washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by size exclusion chromatography (Sephadex, LH20. GE Healthcare, CH2Cl2/MeOH 50/50) to give compound 12 (88%) in the form of a yellow oil. (0287) 1H NMR (300 MHz, CDCl3) delta (ppm) 1.45 (s, 36H, 4 tBu), 2.24 (bs., 1H, H alkyne), 2.30-3.00 (m, 24H, 4 CH2COOtBu, 6 CH2CONH PAMAM, 2 CONHCH2CH2NHCO), 3.10-3.71 (m, 88H, CH2N and NCH2 PAMAM, CH2O, 4 CONHCH2CH2O), 3.79 (m, 2H, CH2 alkyne), 5.30 (m, 2H, NH), 7.20 (m, 4H, NH); 13C NMR (75 MHz, CDCl1) delta (ppm) 173.2, 170.9, 170.7, 80.3, 73.9, 70.4, 70.3, 70.2, 70.0, 69.9, 69.2, 52.7, 50.5, 49.0, 39.9, 39.1, 36.0, 33.1, 27.9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate, and friends who are interested can also refer to it.

Reference:
Patent; UNIVERSITE DE STRASBOURG; UNIVERSITE CLAUDE BERNARD LYON 1; HOSPICES CIVILS DE LYON; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE -CNRS; FELDER-FLESCH, Delphine; BILLOTEY, Claire; PARAT, Audrey; GAROFALO, Antonio; KRYZA, David; JANIER, Marc; (138 pag.)US2016/221992; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 99548-54-6 as follows. 99548-54-6

A solution of methyl 3-bromo-2-methylbenzoate (from for example AstaTech, 24.35 g, 106 mmol) in benzene (300 mL) was treated with N-bromosuccinimide (22.7 g, 128 mmol) followed by benzoyl peroxide, 95% (1.3 g, 5.35 mmol). The reaction mixture was flushed with nitrogen and kept under nitrogen. The reaction mixture was heated at 80C for 2 days. The reaction mixture was concentrated under reduced pressure and treated with hexanes (200 mL). The resulting solids were filtered off, washed with hexanes then with 25% EtOAc / hexanes. The filtrate was concentrated under reduced pressure and the residue was absorbed directly onto silica gel. The product was purified by chromatography (ISCOCombiflash, 330 g, 200 ml/min, 0-8.7% EtOAc / Hexanes over 30 minutes) to yield the title compound (32.4 g, 105 mmol, 99% yield) as an orange liquid. LC/MS: RT= 1.13 min, m/z = 226.8/228.9.

According to the analysis of related databases, 99548-54-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; HARLING, John David; NEIPP, Christopher E.; PENDRAK, Israil; SMITH, Ian Edward David; TERRELL, Lamont Roscoe; YOUNGMAN, Mark; (120 pag.)WO2017/46036; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

369-26-6, name is Methyl 3-amino-4-fluorobenzoate, 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. 369-26-6

Step 1 : 3-Amino-N-(2-tert-butoxyethyl)-4-fluorobenzamide A mixture comprising 2-tert-butoxyethanamine (1 .2 g, 5.12 mmol, 50percentw/w) and methyl 3-amino-4-fluorobenzoate (0.866 g, 5.12 mmol) in THF (10 ml) was treated with TBD (0.713 g, 5.12 mmol) and heated at 90 ¡ãC for 16 hrs. After cooling to RT, the solvent was removed in vacuo and the residue was partitioned between water and EtOAc. The organic portion was separated and washed with 10percent aq citric acid (x 2), NaHC03(sat. aq), brine, dried (MgS04) and concentrated in vacuo. Purification of the crude product by chromatography on silica eluting with 0-100percent EtOAc in iso- hexane afforded the title compound as a clear oil;LC-MS: Rt 1.09 mins; MS m/z 255 [M+H]+; Method 2minl_C_v003

Statistics shows that 369-26-6 is playing an increasingly important role. we look forward to future research findings about Methyl 3-amino-4-fluorobenzoate.

Reference:
Patent; NOVARTIS AG; IRM LLC; BRUCE, Ian; CHAMOIN, Sylvie; COLLINGWOOD, Stephen Paul; FURET, Pascal; FURMINGER, Vikki; LEWIS, Sarah; LOREN, Jon Christopher; MOLTENI, Valentina; SAUNDERS, Alex Michael; SHAW, Duncan; SVIRIDENKO, Lilya; THOMSON, Christopher; YEH, Vince; JANUS, Diana; WEST, Ryan; WO2013/30802; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

3196-15-4, These common heterocyclic compound, 3196-15-4, name is Methyl 2-bromobutyrate, 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.

Example 1Preparation of methyl 2-(6-methoxy-lH-inden-3-yl) butanoateAn oven dried 5 -L four-necked round -bottomed flask was fitted with a thermometer, a condenser, an addition funnel, and a mechanical stirrer. Under Ar protection, a suspension of 5-methoxy-l-indanone (80.0 g, 494 mmol), Zn powder (Lancaster, 56.2 g, 865 mmol) in 2 L anhydrous TEtaF was stirred at 6O0C (internal temperature), while a solution of methyl bromobutyrate (134.1 g, 74] mmoi) in 400 inL anhydrous TEtaF was added slowly through an addition funnel After completion of the addition, the reaction mixture was stirred at 6O0C (internal temperature) for 1 hour. The reaction was followed by TLC analysis of aliquots following IN aqueous HCl work-up. After the reaction was completed, it was cooled in an ice-water bath followed by slow addition of 3 L of IN HCl solution. The pot temperature was kept below 2O0C. The mixture was then extracted with 1 L EtOAc. The organic layer was washed with water until pH 6.0-7.0, then saturated NaCl solution, and dried over Na2SO4, The product (127 g, >;99%), a yellow oil, was obtained after solvent removal and drying under vacuum. 1H NMR (DMSO-t,) delta 7.28(d, IH), 7.05(d, IH), 6.82(dd, IH), 6.22(s, IH), 3.72(s, 3H), 3.60(m, IH), 3.58(s, 3H), 3.28(s, 2H), 1.95(m, IH), 1.80(m, IH), 0.88(t, 3H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 3196-15-4.

Reference:
Patent; DARA BIOSCIENCES, INC.; DELMEDICO, Mary Katherine; WO2010/141696; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

59247-47-1, These common heterocyclic compound, 59247-47-1, name is tert-Butyl 4-bromobenzoate, 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 50-mL round-bottom flask was added (1 S,4S,.5R)-.5-[[5-cyclopropyl-3-(2,6-dichlorophenyl)- L2-oxazol-4-yl]methoxy]-2-azabicyclo[2.2.1 ]heptane 12d (800 mg, 2.11mmol, 1.0 equiv.), tert-buty 4-bromobenzoate 52b (650 mg, 2.53 mmol, 1.20 equiv.),Pd2(dba)3 (190 mg, 0.21 mmol, 0.10 equiv.), BINAP (130 mg, 0.21 mmol, 0.10 equiv),Cs2C01 (960 mg, 2.9.5 mmoL 1.40 equiv.), and toluene (.5 mL) and the resulting mixture was20 stirred at 110 ¡ãC overnight. After cooling to room temperature, l 00 mL of I-hO v.¡¤as addedand the aqueous mixture was extracted with ethyl acetate (l 00 mL x 2). Tiw combinedorganic extracts were washed with brine (100 mL x 2), dried over anbydrous sodium sulfate,filtered, and concentrated under reduced pressure. The residue was purified by silica gelcolumn chromatography eluting vvith ethyl acetate/petroleum ether (1 :6) to give 0.55 g (4Tpercent)25 of tert-buiyl 4-[(1 S,4S,5R)-.5-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-l ,2-oxazol-4-yl]methoxy ]-2-azabicyclo[2.2.1 ]heptan-2-yl]benzoate 52c as a light green solid.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 59247-47-1.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (582 pag.)WO2018/39386; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 369-26-6, name is Methyl 3-amino-4-fluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 369-26-6

To a suspension of compound 21 (1.01 g, 6 mmol) in hydrochloric acid (13 ml, 37%) at 0 C was added a cold solution of sodium nitrite (0.50 g, 7.2 mmol) in water (5 ml) maintaining the temperature below 5 C. The resultant solution was stirred in an ice bath for 30 min before the addition of a solution of tin(II) chloride dihydrate (4.06 g, 18 mmol) in hydrochloric acid (5 ml, 37%) maintaining the temperature below 5 C. The resultant suspension was stirred at 0 C for 3 h and the suspension filtered and then dissolved in DCM, washed with saturated NaHCO3, dried over by MgSO4 to get the compound 22 (1.01 g, 92%). 1H NMR (CDCl3, 400 MHz): delta 7.79-7.77 (m, 1H), 7.46 (s, 1H), 7.04-6.99 (m, 1H), 5.48 (br, 1H), 3.91 (s, 3H) 3.62 (br, 2H). ESI-HRMS: m/z calcd for C8H9FN2O2 [M+H]+ 185.0682 found 185.0664.

The synthetic route of 369-26-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lu, Chaocao; Htan, Bu; Fu, Shitao; Ma, Chunmiao; Gan, Quan; Tetrahedron; vol. 75; 30; (2019); p. 4010 – 4016;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 1186-73-8, name is Trimethyl methanetricarboxylate, 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. 1186-73-8

Step 2: Methyl 10-(((tert-butyldimethylsilyl)oxy)methyl)- l-(2,4-dimethoxybenzyl)-4-hydroxy-9-methyl-2-oxo- 1,2,5, 6,7, 9-hexahydropyrido[3′,2′:6,7]cyclohepta[l,2-f]indole-3-carboxylate Crude N-(2-((tert-butyldimethylsilyloxy)methyl)- l-methyl-6,7,8,9-tetrahydrocyclohepta[f]indol-5(lH)-ylidene)-l-(2,4-dimethoxyphenyl)methanamine (10.6 g, 20.91 mmol) and trimethyl methanetricarboxylate (6.80 g, 35.76 mmol) were mixed together in Ph20 (40 mL). The stirred mixture was placed onto a pre-heated heat block at 230 C and heated for 10 min after initial bubbling of MeOH was observed (occurs at approx. 160 C internal reaction temperature). The reaction mixture was cooled to room temperature, loaded directly on a silica column, eluted first with hexanes to separate Ph20 and then anEtOAc/hexanes gradient (0-80%) to yield the product as a yellow foam (7.44 g, 56% 2 steps). LC-MS: 633.5 [M+H]+, RT 1.85 min. 1H NMR (500 MHz, CDC13) 5 ppm 0.08 (s, 3H), 0.09 (s, 3H), 0.90 (s, 9H), 1.45 – 1.55 (m, IH), 1.85 – 1.95 (m, IH), 1.96 – 2.05 (m, IH), 2.32 -2.44 (m, IH), 2.58 (dd, J=13.4, 6.1 Hz, IH), 2.96 (dd, J=13.4, 5.4 Hz, IH), 3.33 (s, 3H), 3.76 (s, 3H), 3.78 (s, 3H), 4.00 (s, 3H), 4.80 (s, 2H), 5.13 – 5.37 (m, 2H), 6.22 (d, J=2.2 Hz, IH), 6.28 (s, IH), 6.34 (dd, J=8.4, 2.2 Hz, IH), 6.81 (d, J=8.4 Hz, IH), 7.06 (s, IH), 7.32 (s, IH), 13.66 (br. s, IH)

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1186-73-8.

Reference:
Patent; PTC THERAPEUTICS, INC.; GERASYUTO, Aleksey, Igorevich; ARNOLD, Michael, A.; CHEN, Guangming; KARP, Gary, Mitchell; QI, Hongyan; TURPOFF, Anthony, A.; WANG, Jiashi; WOLL, Matthew, G.; ZHANG, Nanjing; ZHANG, Xiaoyan; BRANSTROM, Arthur, A.; NARASIMHAN, Jana; DUMBLE, Melissa, L.; HEDRICK, Jean; WEETALL, Marla, L.; (229 pag.)WO2016/25932; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

63106-93-4, name is 1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one, 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. 63106-93-4

Diethylamine (1 .56 g, 21 .3 mmol) is added dropwise to a suspension of aluminum trichloride (1 .38 g, 10.4 mmol) in toluene (9.6 mL), cooled to 0 C under magnetic stirring and in nitrogen atmosphere, checking that the internal temperature of the system does not exceed 15 C. The obtained solution is maintained at 25 C for about 30 minutes, then a toluene (2 mL) solution of lactone A (1 .50 g, 8.6 mmol) is slowly added. The mixture is maintained under magnetic stirring at 25 C up to complete conversion (about 2 hours), then poured into water (7.2 mL) previously cooled to 5 C, checking that the internal temperature does not exceed 25 C. The obtained phases are separated and the aqueous phase extracted with toluene. The organic phase is filtered on a panel of activated carbon and celite, and concentrated at reduced pressure until a residue of 2.50 g (containing about 2.10 g of the desired product) is obtained, which is used in the next step without any further purification.

Statistics shows that 63106-93-4 is playing an increasingly important role. we look forward to future research findings about 1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one.

Reference:
Patent; QUIMICA SINTETICA, S.A.; BARRECA, Giuseppe; ROMANO’, Bruno Gaetano; (16 pag.)WO2016/71303; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

623-70-1, 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. 623-70-1, name is Ethyl (E)-but-2-enoate, A new synthetic method of this compound is introduced below.

To a round bottom flask containing ethyl (2E)-but-2-enoate (10.9 g, 87.6 mmol) and CCl 4 (100 mL) were added NBS (17 g, 96 mmol) and AIBN (4.3 g, 26 mmol). The reaction mixture was stirred at 80 for 12 h. The reaction mixture was diluted with DCM and extracted with saturated NaHCO 3, water, and brine. The organic layer was dried over anhydrous Na 2SO 4 and evaporated to dryness to yield the title compound (7.5 g, 44% yield) as an oil.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; CAI, Min; ARORA, Nidhi; BACANI, Genesis M.; BARBAY, Joseph Kent; BEMBENEK, Scott D.; CHEN, Wei; DECKHUT, Charlotte Pooley; EDWARDS, James P.; GHOSH, Brahmananda; HAO, Baoyu; KREUTTER, Kevin D.; LI, Gang; TICHENOR, Mark S.; VENABLE, Jennifer D.; WEI, Jianmei; WIENER, John J. M.; WU, Yao; ZHU, Yaoping; ZHANG, Feihuang; ZHANG, Zheng; XIAO, Kun; (999 pag.)WO2018/103058; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

6962-92-1, These common heterocyclic compound, 6962-92-1, name is 4-Chlorobutyl acetate, 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.

Examples 2 to 13 The process of Example 1 was repeated in a similar manner except that 0.4 mmol of each of the boron compounds as shown in Table 1 was used in place of p-methoxyphenylboronic acid and 0.30 mmol of each organic halide as shown in Table 1 was used in place of 1-bromooctane and reaction was conducted for the noted period of time in Table 1.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 6962-92-1.

Reference:
Patent; Sumitomo Chemical Co.,Ltd.; EP1439157; (2004); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics