Some tips on 95715-86-9

95715-86-9 Methyl (R)-N-Boc-2,2-dimethyloxazolidine-4-carboxylate 688220, aoxazolidine compound, is more and more widely used in various.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.95715-86-9,Methyl (R)-N-Boc-2,2-dimethyloxazolidine-4-carboxylate,as a common compound, the synthetic route is as follows.

95715-86-9, To a dry THF solution containing compound 23 (2.5 g,11 mmol), which was prepared from L-serine via step a and areduction by NaBH4, LiCl/dry THF, 0.5 g (20 mmol) of NaH was added. After stirring for 5 min, 3.4 g (22 mmol) of iodoethanewas added. After stirring for 10 h at ambient temperature, 1 mLof H2O was added to the reaction mixture, the solvent wasremoved in vacuo, and the resulting residue was purified by columnchromatography (hexane/ethyl acetate = 4:1) to afford 24 asan oil (1.3 g, 47%).

95715-86-9 Methyl (R)-N-Boc-2,2-dimethyloxazolidine-4-carboxylate 688220, aoxazolidine compound, is more and more widely used in various.

Reference£º
Article; Nagaoka, Hikaru; Nishiwaki, Hisashi; Kubo, Takuya; Akamatsu, Miki; Yamauchi, Satoshi; Shuto, Yoshihiro; Bioorganic and Medicinal Chemistry; vol. 23; 4; (2015); p. 759 – 769;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

 

Some tips on 95715-86-9

95715-86-9 Methyl (R)-N-Boc-2,2-dimethyloxazolidine-4-carboxylate 688220, aoxazolidine compound, is more and more widely used in various.

95715-86-9,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.95715-86-9,Methyl (R)-N-Boc-2,2-dimethyloxazolidine-4-carboxylate,as a common compound, the synthetic route is as follows.

To a solution of (S)-2, 2-Dimethyl-oxazolidine-3, 4-dicarboxylic acid 3-tert-butyl ester 4-methyl ester (435 mg, 1.678 mmol) in THF (5 ml) under nitrogen atmosphere was added 1 N-LiAIH4 (5 ml, 5.033 mmol) at degrees C and the mixture was stirred at room temperature for 1 h. The mixture was quenched with water and 10% NaOH solution, filtered through celite. The filtrate was diluted with EtOAc and washed with brine, dried over MgS04, filtered, and concentration in vacuo. The obtained residue was purified by flash chromatography eluting with 5: 1 Hexane/Ethyl acetate to give the (R)-4-Hydroxymethyl-2, 2-dimethyl- oxazolidine-3-carboxylic acid ter-butyl ester (383 mg, 99%) as a white solid. To a solution of (R)-4-Hydroxymethyl-2, 2-dimethyl-oxazolidine-3-carboxylic acid ter-butyl ester (383 mg, 1.656 mmol) in anhydrous pyridine (4 ml) under nitrogen atmosphere was added tosyl chloride (631 mg, 3.312 mmol) at 0 degrees C and the mixture was stirred for 24 h. The reaction mixture was concentrated under reduced pressure and diluted with EtOAc, washed with brine, dried over MgS04, filtered, and concentrated. Recrystallization from EtOAc-n-hexane to give the title compound (554 mg, 87%). 1H-NMR (300MHz, CDCI3) : 1.40 (s, 9H), 1.54 (s, 3H), 2.45 (s, 3H), 3.78-4. 20 (m, 5H), 7.40 (d, 2H), 7.81 (d, 2H); MS (ESI+) : 408 ([M+Na] +).

95715-86-9 Methyl (R)-N-Boc-2,2-dimethyloxazolidine-4-carboxylate 688220, aoxazolidine compound, is more and more widely used in various.

Reference£º
Patent; CHUGAI SEIYAKU KABUSHIKI KAISHA; WO2005/87700; (2005); A2;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

 

Some tips on 95715-86-9

95715-86-9 Methyl (R)-N-Boc-2,2-dimethyloxazolidine-4-carboxylate 688220, aoxazolidine compound, is more and more widely used in various.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.95715-86-9,Methyl (R)-N-Boc-2,2-dimethyloxazolidine-4-carboxylate,as a common compound, the synthetic route is as follows.,95715-86-9

A solution of LiOH (0.046 g, 1.928 mmol) in water (2 mL) was added to a solution of (S)-3-tert-butyl 4-methyl 2,2-dimethyloxazolidine-3,4-dicarboxylate (0.5 g, 1.928 mmol) in THF (6 mL). The resulting mixture was stirred at rt for 48 h, acidified to pH 4 with a 1 N aqueous solution of hydrochloric acid and extracted three times with ethyl acetate. The combined organic phases were dried (MgSO4), filtered and concentrated under vacuum to afford Cap L-25 (0.2 g) as a yellow oil. Used without further purification.1H NMR (400 MHz, DMSO-d6, mixture of rotomers) delta 12.72 (br. s., 1H), 4.33-4.23 (m, 1H), 4.18-4.09 (m, 1H), 3.93 (dt, J=9.0, 3.3 Hz, 1H), 1.56-1.51 (m, 3H), 1.42 (s, 7H), 1.39-1.33 (m, 6H);13C NMR (101 MHz, DMSO-d6, mixture of rotomers) delta 172.32-171.83 (m), 150.7, 93.76-93.42 (m), 79.66-79.01 (m), 65.94-65.54 (m), 58.79-58.57 (m), 28.05-27.74 (m, 3C), 24.93-24.75 (m), 24.16-23.99 (m).

95715-86-9 Methyl (R)-N-Boc-2,2-dimethyloxazolidine-4-carboxylate 688220, aoxazolidine compound, is more and more widely used in various.

Reference£º
Patent; Hewawasam, Piyasena; Lopez, Omar D.; Tu, Yong; Wang, Alan Xiangdong; Xu, Ningning; Kadow, John F.; Meanwell, Nicholas A.; Gupta, Samayamuthula Venkata Satya Arun Kumar; Kumar, Indasi J. Gopi; Ponugupati, Suresh Kumar; Belema, Makonen; US2015/23913; (2015); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

 

Brief introduction of 95715-86-9

The synthetic route of 95715-86-9 has been constantly updated, and we look forward to future research findings.

95715-86-9, Methyl (R)-N-Boc-2,2-dimethyloxazolidine-4-carboxylate is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

6.1 g (23.36 mM) of 3- (1,1-dimethylethyl) -4-methyl- (S) -2,2-dimethyloxazolidin-3,4-dicarboxylate was dissolved in 12 ml of tetrahydrofuran solution was added 1.4 g (37 mM) of sodium borohydride,Was suspended in 12 ml of tetrahydrofuran solution and suspended dropwise over 30 minutes at room temperature.After dropwise addition, cool the reaction solution to 0 ~ 5 .To this mixed solution, a boron trifluoride diethyl ether solution32 ml (265.8 mM) of 10 ml of a tetrahydrofuran solutionIs added and the mixture is heated. Reflux for 6 hours. After confirming that the reaction progress was completed by TLC, then cool to 0 ~ 5 .20 ml of a tetrahydrofuran solution is added to the reaction mixture, stirred at the same temperature for 30 minutes, and then filtered.12 ml of distilled water: tetrahydrofuran solution (1: 1) was added to the filtrate,Were added dropwise at the same temperature, 13.7 g (343 mM) of caustic soda,Is dissolved in a small amount of distilled water, and the mixture is heated and refluxed for 2 hours.After confirming the completion of the reaction by TLC, the reaction mixture is cooled to room temperature.The filtrate was subjected to filtration to concentrate the filtrate tetrahydrofuran solution under reduced pressureRemove.100 ml of distilled water was added to the concentrated residue,Wash with 20 ml X 2 of isopropyl ether.The aqueous layer was extracted with 150 ml of methylene chloride x 3 timesThe next organic layers were combined and washed with 50 ml of purified water,The organic layer was dried over anhydrous magnesium sulfate, filtered,The methylene chloride was removed by concentration under reduced pressure to give the title compound5.2 g (96%) was obtained.

The synthetic route of 95715-86-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MC Chem Co.,Ltd; Kim, Moon Sik; Kim, Hwe Nam; Kim, Hay Jin; Kwon, Junga; Yun, Ji Hay; (21 pag.)KR2015/31544; (2015); A;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

 

Brief introduction of 95715-86-9

The synthetic route of 95715-86-9 has been constantly updated, and we look forward to future research findings.

95715-86-9, Methyl (R)-N-Boc-2,2-dimethyloxazolidine-4-carboxylate is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of LiOH (0.046 g, 1.928 mmol) in water (2 mL) was added to a solution of (S)-3-tert-butyl 4-methyl 2,2-dimethyloxazolidine-3,4-dicarboxylate (0.5 g, 1.928 mmol) in THF (6 mL). The resulting mixture was stirred at rt for 48 h, acidified to pH 4 with a 1 N aqueous solution of hydrochloric acid and extracted three times with ethyl acetate. The combined organic phases were dried (MgSO4), filtered and concentrated under vacuum to afford Cap L-25 (0.2 g) as a yellow oil. Used without further purification.1H NMR (400 MHz, DMSO-d6, mixture of rotomers) delta 12.72 (br. s., 1H), 4.33-4.23 (m, 1H), 4.18-4.09 (m, 1H), 3.93 (dt, J=9.0, 3.3 Hz, 1H), 1.56-1.51 (m, 3H), 1.42 (s, 7H), 1.39-1.33 (m, 6H);13C NMR (101 MHz, DMSO-d6, mixture of rotomers) delta 172.32-171.83 (m), 150.7, 93.76-93.42 (m), 79.66-79.01 (m), 65.94-65.54 (m), 58.79-58.57 (m), 28.05-27.74 (m, 3C), 24.93-24.75 (m), 24.16-23.99 (m).

The synthetic route of 95715-86-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Hewawasam, Piyasena; Lopez, Omar D.; Tu, Yong; Wang, Alan Xiangdong; Xu, Ningning; Kadow, John F.; Meanwell, Nicholas A.; Gupta, Samayamuthula Venkata Satya Arun Kumar; Kumar, Indasi J. Gopi; Ponugupati, Suresh Kumar; Belema, Makonen; US2015/23913; (2015); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

 

New learning discoveries about 95715-86-9

As the paragraph descriping shows that 95715-86-9 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.95715-86-9,Methyl (R)-N-Boc-2,2-dimethyloxazolidine-4-carboxylate,as a common compound, the synthetic route is as follows.

Example 6. Synthesis of (4S)-4-(morpholin-4-ylcarbonyl)-3-{4-[(trans-3- piperidin-1 -ylcyclobutyl)oxy]phenyl}-1 ,3-oxazolidin-2-one 18.; 6.1. Synthesis of (4S)-3-(tert-butoxycarbonyl)-2,2-dimethyl- 1 ,3-oxazolidine-4- carboxylic acid a61.; Lithium hydroxide (277 mg, 1 1.5 mmol, 1 eq) is added to a solution of methyl 3-tert-butyl 4- methyl (4S)-2,2-dimethyl-1 ,3-oxazolidine-3,4-dicarboxylate a60 (3 g, 1 1.5 mmol, 1 eq) in a tetrahydrof u ran/water mixture (23 ml/11 ml). The mixture is stirred at room temperature for 2 days, acidified to pH 4 with a 1 N aqueous solution of hydrochloric acid and extracted three times with ethyl acetate. The combined organic phases are dried over magnesium sulfate and concentrated under vacuum to afford 2.79 g of (4S)-3-(tert-butoxycarbonyl)- 2,2-dimethyl-1 ,3-oxazolidine-4-carboxylic acid a61 as a yellow oil. Yield: 99 %.LC-MS (MH+): 246.

As the paragraph descriping shows that 95715-86-9 is playing an increasingly important role.

Reference£º
Patent; UCB PHARMA S.A.; WO2008/128919; (2008); A2;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

 

Analyzing the synthesis route of 95715-86-9

The synthetic route of 95715-86-9 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.95715-86-9,Methyl (R)-N-Boc-2,2-dimethyloxazolidine-4-carboxylate,as a common compound, the synthetic route is as follows.

A solution of 3-tert-butyl 4-methyl (4S)-2,2-dimethyl-1,3-oxazolidine-3,4-dicarboxylate (10 g, 38.565 mmol, 1.00 equiv), NaBH4 (2.92 g, 77.130 mmol, 2.00 equiv), MeOH (30 mL), and CaCl2 (12.84 g, 115.695 mmol, 3.00 equiv) in THF (150 mL) was stirred for 1 h at RT. The reaction was quenched by the addition of 30 mL of water, extracted with 3¡Á100 mL of EtOAc, dried over anhydrous sodium sulfate and concentrated under vacuum to afford 9.38 g of the title compound as a yellow oil LCMS (ESI, m/z): 232.15 [M+H]+.

The synthetic route of 95715-86-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Ribon Therapeutics Inc.; Vasbinder, Melissa Marie; Schenkel, Laurie B.; Swinger, Kerren Kalai; Kuntz, Kevin Wayne; (410 pag.)US2019/330194; (2019); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

 

Downstream synthetic route of 95715-86-9

As the paragraph descriping shows that 95715-86-9 is playing an increasingly important role.

95715-86-9, Methyl (R)-N-Boc-2,2-dimethyloxazolidine-4-carboxylate is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of LiOH (0.046 g, 1.928 mmol) in water (2 mL) was added to a solution of (S)-3-tert-butyl 4-methyl 2,2-dimethyloxazolidine-3,4-dicarboxylate (0.5 g, 1.928 mmol) in THF (6 mL). The resulting mixture was stirred at rt for 48 h, acidified to pH 4 with a 1 N aqueous solution of hydrochloric acid and extracted three times with ethyl acetate. The combined organic phases were dried (MgS04), filtered and concentrated under vacuum to afford Cap L-25 (0.2 g) as a yellow oil. Used without further purification.XH NMR (400MHz, DMSO-d6, mixture of rotomers) delta 12.72 (br. s., 1H), 4.33 – 4.23 (m, 1H), 4.18 – 4.09 (m, 1H), 3.93 (dt, J=9.0, 3.3 Hz, 1H), 1.56 – 1.51 (m, 3H), 1.42 (s, 7H), 1.39 – 1.33 (m, 6H);13C MR (101MHz, DMSO-d6, mixture of rotomers) delta 172.32 – 171.83 (m), 150.7, 93.76 – 93.42 (m), 79.66 – 79.01 (m), 65.94 – 65.54 (m), 58.79 – 58.57 (m), 28.05 – 27.74 (m, 3C), 24.93 – 24.75 (m), 24.16 – 23.99 (m)

As the paragraph descriping shows that 95715-86-9 is playing an increasingly important role.

Reference£º
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;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem