Category: 915095-89-5

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.915095-89-5,(S)-3-(4-(5-Bromo-2-chlorobenzyl)phenoxy)tetrahydrofuran,as a common compound, the synthetic route is as follows.

915095-89-5, Under a nitrogen atmosphere, dry THF (60 mL) was added to a 500 mL three-neck flask, cooled to -10C, n-BuMgCl¡¤LiCl in THF (27.2 mL, 27.2 mmol) and a n-BuLi solution in n-hexane were added ( 21.8 mL, 54.4 mL), stirring for 10 min.(S)-4-Bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene (10.0 g, 27.2 mmol) was dissolved in dry THF (20 mL) and slowly added dropwise The reaction solution was maintained at -10C and the reaction was stirred for 2.0 h.After the reaction was completed, a solution of 2,3,4,6-tetraacetoxy-alpha-D-glucopyranose bromide (3.0 g, 6.2 mmol) in THF (20 mL) was slowly added dropwise, and the reaction was continued at -10 C. for 3.0 h. After the reaction was completed, a solution of methanesulfonic acid (9.3 mL) in methanol (80 mL) was added and the temperature was raised to 25 C. for 18.0 h.Adjust the pH to about 7 with saturated NaHCO3 solution and extract twice with EA (100 mL).The organic phase was washed successively with water (100 mL) and saturated NaCl solution (100 mL). Anhydrous MgSO4 was added and the mixture was filtered. The filtrate was concentrated to dryness under reduced pressure to give a pale yellow oil III (15.6 g). The yield was 92.6%.

The synthetic route of 915095-89-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; China Pharmaceutical Group Sichuan Antibiotic Industry Institute; Shi Kejin; Chen Lin; Li Jianghong; Gou Xiaojun; Ren Fengying; Yang Chen; (8 pag.)CN107556302; (2018); A;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

915095-89-5, (S)-3-(4-(5-Bromo-2-chlorobenzyl)phenoxy)tetrahydrofuran is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Add Compound C-2 (10 g, 27.2 mmol) to a 250 mL three-necked flaskAnd 70mL of tetrahydrofuran, stir and dissolve.The resulting solution is cooled to -70 to -80 C,Slowly add n-butyllithium solution (2.5M THF solution) to the cooled solution.12.5 mL, 1.15 eq), and stirred at -70 to -80 C for 1 hour.Further, a solution of the compound B in tetrahydrofuran (8.5 g of B in 30 mL of tetrahydrofuran, 31.3 mmol, 1.15 eq) was added dropwise to the reaction mixture.The mixture was stirred at -70 to -80 C for 2 hours. The reaction solution is heated to -10 to 0 C.The reaction solution was diluted with a saturated aqueous solution of NH 4Cl (20 mL).Add ethyl acetate(100 mL ¡Á 2) The reaction quenching solution was extracted twice, and the ethyl acetate layer was combined.The organic layer was washed with saturated brine (100 mL).The organic layer was concentrated to dryness under reduced pressure at 40 to 50 C.The resulting solid was recrystallized from ethyl acetate and n-hexane.Having 11.4g of compoundD-2, yield 88.4%.

As the paragraph descriping shows that 915095-89-5 is playing an increasingly important role.

Reference£º
Patent; Zhejiang Hongyuan Pharmaceutical Co., Ltd.; Wang Haibo; Mei Guangyao; Jin Hui; Zhang Wei; Liu Xuesheng; Lin Wenjing; Wang Kaiming; (20 pag.)CN108675976; (2018); A;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

915095-89-5, (S)-3-(4-(5-Bromo-2-chlorobenzyl)phenoxy)tetrahydrofuran is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 50 gm of (S)-4-bromo-l-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)- benzene in tetrahydrofuran 300 mL and toluene 100 mL was cooled to -90 C to -100 C, 90 mL of n-hexyl Lithium (33% in tetrahydrofuran) was gradually added and the solution was stirred for 15 to 30 min. Then a solution of 2, 3, 4, 6 -tetrakis-0-(trimethylsilyl)-D- glucopyranone in toluene was added at -90 C to -100 C and the reaction mixture was stirred for 2 to 5 hrs. Thereafter 200 mL solution of methanesulphonic acid in methanol was added to the reaction mixture at -70 C to -90 C, the temperature of the reaction mixture was raised to 0 C to 15 C and the reaction mixture was stirred for 10 to 15 hrs at ambient temperature. The solution was then quenched with 8% aq. sodium bicarbonate solution followed by layer separation. The aqueous layer was extracted with ethylacetate (2 X 250 mL).The combined organic layer was washed with 250 mL 10% brine solution. The combined organic layer was concentrated under vacuum followed by stripping with acetonitrile 50mL to afford 95 gm of crude intermediate compound of formula (IV) as an oily mass. 200 mL of dichloromethane and 100 mL of acetonitrile was added to the oily mass at -30 C to -40 C followed by addition of trimethylsilane and borontrifluoride etherate. The reaction mixture was stirred for 2 to 3 hrs followed by addition of 550 mL of 8% aq. sodium bicarbonate solution at 5 C to 20 C. The organic layer was separated and extracted with dichloromethane (I X 250 mL and 1 X 100 mL). The combined organic layer was concentrated to get an oily mass of compound of formula (V). A solution of compound of formula (V) in 200 mL dichloromethane was added to slurry of 50 gm L-proline in 200 mL isopropanol and heated at 40 oC to 50 C for 7-10 hrs. The reaction mixture was filtered and washed with 25 mL dichloromethane and dried under vacuum to afford 53 gm of crystalline Form A of Empagliflozin L-proline complex.

The synthetic route of 915095-89-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; LUPIN LIMITED; AGARKAR, Amit, Madan; MITRA, Rangan; RANANAWARE, Umesh, Babanrao; GODBOLE, Himanshu, Madhav; SINGH, Girij, Pal; (27 pag.)WO2017/141202; (2017); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem