Tag: M.W=100-200

A common compound: 10047-10-6, name is Methyl 2-aminopentanoate hydrochloride, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 10047-10-6

EXAMPLE 11 Synthesis of METHYL N-F (4 -IODOBIPHENYL-4-YL) CARBONYLL-L-LEUCYLNORVALINATE Methyl N [ (4′-iodobiphenyl-4-yl) carbonyl]-L-leucinate (22.5 g, 50 mmoles) in 100 mL of tetrahydrofuran, 40 ML of methanol and 10 mL of water is treated with a suspension of lithium hydroxide monohydrate (3.15 g, 75 mmoles) in 20 mL of boiling water. The reaction was stirred until completion as judged by TLC. Reaction was carefully adjusted to pH 4 approximately by addition of 1 N HCl and most of the solvents were removed under reduced pressure. The concentrated suspension was diluted with dichloromethane (200 ML) and 1 N HCl (150 ML). The phases were separated and the aqueous phase was washed with dichloromethane (150 mL). The combined organic layers were dried over magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in DIMETHYLFORMAMIDE (100 mL) and treated with racemic norvaline hydrochloride (8.6 g, 51 moles) followed by HATU (19.6 g, 51 mmoles). After one minute, triethylamine (17.5 mL, 125 mmoles) was added and the reaction stirred overnight. The reaction medium was diluted with ethyl acetate (300 ML), diethyl ether (100 ML) and IN hydrochloric acid (300 ML). The phases were separated and the organic phase was washed with 0.1 N hydrochloric acid (200 mL), two 200-ML portions of water and brine (100 ML). The organic phase was dried over magnesium sulfate and concentrated under reduced pressure to obtain a solid which was purified by trituration in ether.

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, 10047-10-6, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK FROSST CANADA & CO.; WO2005/28424; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

6962-92-1, name is 4-Chlorobutyl acetate, 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. 6962-92-1

84.5 g of ethyl 4-hydroxybenzoate, 84.2 g of 4-chlorobutyl acetate, 105 g of potassium carbonate and 254 g of N, N-dimethylacetamide were mixed, and the resulting mixture was heated to 100C and stirred. After cooling, methyl isobutyl ketone was added to the reaction mixture, and the mixture was washed with water and then the solvent was removed to obtain 126 g of an oily substance containing the compound (i) as a main component. Yield: 88% (based on ethyl 4-hydroxybenzoate).

Statistics shows that 6962-92-1 is playing an increasingly important role. we look forward to future research findings about 4-Chlorobutyl acetate.

Reference:
Patent; Sumitomo Chemical Co. Ltd.; Ochial, Koshiro; Kobayashi, Tadahiro; (34 pag.)KR101677764; (2016); B1;,
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 6065-82-3 as follows. 6065-82-3

(i) 2,2-Diethoxyacetamide(See, for example, Inami, K., Shiba, T., Bull. Chem. Soc. Jpn., 1985, 58, 352.) Ethyl diethoxyacetate (Aldrich) (10 mL, 56.41 mmol) was added to concentratedNH4OH (50 mL) and the mixture allowed to stir until a homogeneous solution was obtained (40 hours). The solvent was then removed under reduced pressure to yield the sub-title compound as fine white needles (8.209 g, 99%). m.p. = 47-51C. vmax KBr/cm”1: 3495, 3298 upsilon(N-H), 2898 upsilon(C-H), upsilon(N-Me) 1673 upsilon(C=O), 1317 delta(C-O). deltaH 1H(CDCl3): 1.11 (6H, t, 2(CH3) (J=8.0Hz)), 4.55 (4H, m, 2(CH2)), 4.64 (IH, s,C-H), 7.25 (2H, d, NH2 (J=I 88.0Hz)).LREIMS: Found 148.00 (M+H) calculated for C6Hi3NO3 147.09.

According to the analysis of related databases, 6065-82-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY OF STRATHCLYDE; WO2008/38018; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

18927-05-4, 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. 18927-05-4, name is Methyl 3-Methoxyphenylacetate, This compound has unique chemical properties. The synthetic route is as follows.

To methyl 2-(3-methoxyphenyl)acetate (Aldrich, 1 g, 5.55 mmol) in THF (10 ml) at 00C, NaHMDS (5.55 ml, 5.55 mmol) was added. After stirring at 00C for 10 min, reaction mixture was stirred at RT for 0.5h and then MeI (0.4 ml) was added. After 45 min, another 5.55 ml of NaHMDS was added at 00C. Again after stirring at RT for 0.5 h, 0.5 ml of MeI was added and the reaction mixture was stirred at RT for 2h. Then the reaction mixture was quenched with ammonium chloride and solvent removed. Then the reaction mixture was diluted with ethyl acetate, acidified with 2N HCl and washed with ether. Aqueous layer was then basified and extracted with CHCl3. organic layer was dried and evaporated to yield methyl 2-(3-methoxyphenyl)-2-methylpropanoate.

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; COMENTIS, INC.; PURDUE RESEARCH FOUNDATION; WO2009/42694; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 178312-47-5, name is Ethyl 4,4-difluorocyclohexanecarboxylate, 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 178312-47-5. 178312-47-5

Example 1 : 4,4-Difluorocyclohexanecarboxamide; A suspension of ethyl 4,4-difluorocyclohexanecarboxylate (2500mg, 13mmol) in ammonium hydroxide (28%, 50 ml) was stirred at 60 C overnight. After removal of solvent, the residue was washed with water. The precipitate was obtained as product (white solid, 800 mg). 1H NMR (300 MHz, CDCl3): delta 5.31-5.45 (br, 2H), 2.02-2.27 (m, 3H), 1.92-2.02 (m, 2H), 1.72- EPO 1.87 (m, 4H). The mother liquor was acidified with IN HCl to pHPatent; ASTRAZENECA AB; NPS PHARMACEUTICALS, INC.; WO2007/21309; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 4630-82-4, name is Methyl cyclohexanecarboxylate, 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. 4630-82-4

60%-NaH (4.65g, 0. 116MOL) was suspended in DME (70mL) and then heated to 70C under reflux. Subsequently, a solution of cyclohexane carboxylic acid methyl ester (5. 00g, 0. 0352MOL) and 2-methyl-3-oxo-butyric acid ethyl ester (90%, 6.20g, 0. 0387MOL) diluted with DME (30mL) was added thereto over 45 minutes and then heated under reflux for 18 hours. After the resulting solution was cooled down to room temperature, the solvent was distilled off under reduced pressure. Then, water (50mL) was added thereto and the resulting solution was stirred for 2 hours. After a 2N HCl solution was added thereto for acidification followed by extraction with ethyl acetate (50MLX 2), the resulting organic layer was washed with a saturated NACI solution (50ML). The organic layer was dried over MGSO4, filtered, and then concentrated under a reduced pressure. The resulting residue was purified by recrystallization from ethyl acetate/n-hexane to obtain white solid (4.80g, 66%). ‘H-NMR (CDCL) ; 6 = 8. 46 (brs, 1H), 6.02 (s, 1H), 2.35 (m, 1H), 1.96 (s, 3H), 1.90- 1. 15 (m, 10H). MS = 209 [M+H], 231 [M+Na]

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 4630-82-4.

Reference:
Patent; C & C RESEARCH LABORATORIES; WO2004/50624; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

14062-24-9, Adding some certain compound to certain chemical reactions, such as: 14062-24-9, name is Ethyl 4-chlorophenylacetate, 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 14062-24-9.

A solution of freshly prepared lithium diisopropylamide (23.0 mL of 0.31M stock solution, 7.13 mmol) cooled to -78 C. was treated with (4-chloro-phenyl)-acetic acid ethyl ester (1.28 g, 6.48 mmol) in tetrahydrofuran/hexamethylphosphoramide (16.1 mL, 3:1). The resulting solution was stirred at -78 C. for 45 min. At this time, the reaction was treated with a solution of iodomethylcyclopentane (1.50 mg, 7.13 mmol) in hexamethylphosphoramide (1 mL). The reaction-mixture was stirred at -78 C. for 4 h. The reaction was warmed to 25 C. and stirred at 25 C. for 16 h. The reaction mixture was then quenched by the dropwise addition of a saturated aqueous ammonium chloride solution (20 mL). This mixture was poured into water (100 mL) and extracted with ethyl acetate (3*50 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 75/25 hexanes/ethyl acetate) afforded 2-(4-chloro-phenyl)-3-cyclopentyl-propionic acid ethyl ester (1.65 g, 90.9%) as a yellow oil: EI-HRMS m/e calcd for C16H21Cl2O2 (M+) 280.1230, found 280.1227.

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 14062-24-9.

Reference:
Patent; Hoffman-La Roche Inc.; US6610846; (2003); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

42726-73-8, A common compound: 42726-73-8, name is tert-Butyl methyl malonate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Example 13 L3-(7-Methoxy-indol-1- lY )-3-pyridin-3- T(at)l-propyll-methyl-aznine The synthetic procedure of Example 12 is outlined in Scheme L below. SCHEME L Step; 2-Pyridin-3-ylmethylene-malonic acid tert-butyl ester methyl ester A mixture of pyridine-3-carboxaldehyde (2.72 g), propanedioic acid, 1,1-dimethylethyl methyl ester (4.42 g), piperidine (0.173 g) and benzoic acid (0.155 g) in benzene (100 ml) was heated at reflux with removal of water to a Dean-Stark trap for 12 hours. The cooled mixture was washed with bicarbonate solution, concentrated under vacuum and the residue was purified by column chromatography, eluting with ethyl acetate – hexane (3 : 7) to afford racemic 2-pyridin-3-ylmethylene-malonic acid tert-butyl ester methyl ester as an oil (3.21 g).

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, tert-Butyl methyl malonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F.HOFFMANN-LA ROCHE AG; WO2005/118539; (2005); 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. 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate, This compound has unique chemical properties. The synthetic route is as follows., 816-27-3

To a solution of ?ran5-l-amino-3-[tert-butyl(dimethyl)silyl]oxy-5-phenyl-pyrrolidin-2-one (7.0 g, 22.8 mmol) in ethanol (150 mL) was added ethyl 2-ethoxy-2-imino-acetate (6.63 g, 45.7 mmol). The reaction mixture was stirred at 60 C for 16 h and subsequently concentrated under reduced pressure to afford crude trans-ethyl 2-(3-((tert-butyldimethylsilyl)oxy)-2-oxo-5-phenylpyrrolidin-l-yl)amino)- 2-iminoacetate (8.50 g, 92%) as a yellow oil, used in the next step without further purification. LCMS RT= 2.154 min, m/z = 406.3 [M + H]+. LCMS (0 to 60% acetonitrile in water + 0.03% trifluoacetic acid over 3.0 mins) retention time 2.143 min, ESI+ found [M+H] = 406.3.

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; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; PATEL, Snahel; HAMILTON, Gregory; ZHAO, Guiling; CHEN, Huifen; DANIELS, Blake; STIVALA, Craig; (358 pag.)WO2019/12063; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 1127-01-1, name is Ethyl 1-hydroxycyclohexanecarboxylate, 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 1127-01-1. 1127-01-1

1. Preparation of Hexylester: Example 1a with Modification (Column 125) 0.1 mol of ethyl-1-hydroxycyclohexanecarboxylate were introduced into 200 ml of absolute methylene dichloride, 0.12 mol of triethylamine (Et3N) were added, and a solution of 0.1 mol of 2-(2,4-dichlorophenyl)acetyl chloride in 50 ml of absolute methylene dichloride was added dropwise at 0-10 C. After the solution had been stirred for 16 h at room temperature, it was washed with aqueous citric acid and aqueous sodium bicarbonate solution, and the organic phase was dried over sodium sulfate and evaporated on a rotary evaporation.

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 Ethyl 1-hydroxycyclohexanecarboxylate.

Reference:
Patent; ROTAM AGROCHEM INTERNATIONAL COMPANY LIMITED; BRISTOW, James Timothy; (13 pag.)US2017/166546; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics