Category: 2133-34-8

Name is (S)-Azetidine-2-carboxylic acid, as a common heterocyclic compound, it belongs to chiral-catalyst compound, and cas is 2133-34-8, its synthesis route is as follows.,2133-34-8

Step A. N-(2-Thiophene-sulfonyl)-azetidine-2(S)-carboxylic Acid To a magnetically stirred mixture of azetidine-2(S)-carboxylic acid (1.0 g, 10 mmol) and Na2CO3 (2.1 g, 20 mmol) in 30 mL of water at 0 C. was added thiophene-2-sulfonyl chloride (1.8 g, 10 mmol), and the reaction was allowed to slowly warm up to room temperature overnight. The reaction was quenched by careful addition of concentrated HCl at 0 C. to pH above 2, and the product was extracted with EtOAc (3*15 mL). The extracts were dried over Na2SO4, and concentrated to dryness to provide the title compound as a white solid, which is >90% pure by 1H-NMR and used without further purification. 400 MHz 1H NMR (CD3OD): delta 2.2-2.4 (m, 2H), 3.7-3.9 (m, 2H), 4.42 (dd, 1H), 7.30 (dd, 1H), 7.75 (dd, 1H), 7.95 (dd, 1H).

With the complex challenges of chemical substances, we look forward to future research findings about (S)-Azetidine-2-carboxylic acid

Reference£º
Patent; Merck & Co., Inc.; US6645939; (2003); B1;,
Chiral Catalysts
Chiral catalysts – SlideShare

Name is (S)-Azetidine-2-carboxylic acid, as a common heterocyclic compound, it belongs to chiral-catalyst compound, and cas is 2133-34-8, its synthesis route is as follows.,2133-34-8

Step A. N-(2-Thiophene-sulfonyl)-azetidine-2(S)-carboxylic Acid To a magnetically stirred mixture of azetidine-2(S)-carboxylic acid (1.0 g, 10 mmol) and Na2CO3 (2.1 g, 20 mmol) in 30 mL of water at 0 C. was added thiophene-2-sulfonyl chloride (1.8 g, 10 mmol), and the reaction was allowed to slowly warm up to room temperature overnight. The reaction was quenched by careful addition of concentrated HCl at 0 C. to pH above 2, and the product was extracted with EtOAc (3*15 mL). The extracts were dried over Na2SO4, and concentrated to dryness to provide the title compound as a white solid, which is >90% pure by 1H-NMR and used without further purification. 400 MHz 1H NMR (CD3OD): delta 2.2-2.4 (m, 2H), 3.7-3.9 (m, 2H), 4.42 (dd, 1H), 7.30 (dd, 1H), 7.75 (dd, 1H), 7.95 (dd, 1H).

With the complex challenges of chemical substances, we look forward to future research findings about (S)-Azetidine-2-carboxylic acid

Reference£º
Patent; Merck & Co., Inc.; US6645939; (2003); B1;,
Chiral Catalysts
Chiral catalysts – SlideShare

As a common heterocyclic compound, it belong chiral-catalyst compound,(S)-Azetidine-2-carboxylic acid,2133-34-8,Molecular formula: C4H7NO2,mainly used in chemical industry, its synthesis route is as follows.,2133-34-8

To a round bottom flask was added (,S)-azetidine-2-carboxylic acid (63, 51 1 mg, 5.05 mmol) and sodium hydroxide (7.0 mL of IN; 7.08 mmol). The reaction was cooled to 0 C and 3,5-dichlorobenzenesulfonyl chloride (65, 1.36 g, 5.56 mmol) was added followed by N,N- diisopropylethylamine (1.0 mL, 5.81 mmol) and acetone (7 mL) and the reaction was stirred overnight at room temperature. The acetone was evaporated and the aqueous layer extracted with diethyl ether (3 x 50 mL). The aqueous layer was adjusted to pH=l using cone. HC1 and then extracted with ethyl acetate (3 x 75 mL). The ethyl acetate layers were pooled, dried using sodium sulfate, filtered and concentrated in vacuo to give product (,S)-l-((3,5- dichlorophenyl)sulfonyl)azetidine-2-carboxylic acid (67, 1.6 g, 100% yield) as a white solid. LC- MS: tR=2.06 min; m/z=309.8, 31 1.9. 1 NHMR (400 MHz, DMSO-d6) delta ppm 13.08 (br. s., 1 H) 8.06 (t, J=1.83 Hz, 1 H) 7.85 (d, J=1.96 Hz, 2 H) 4.63 (dd, J=9.54, 7.58 Hz, 1 H) 3.67 – 3.88 (m, 2 H) 2.29 – 2.42 (m, 1 H) 2.13 – 2.28 (m, 1 H).

With the synthetic route has been constantly updated, we look forward to future research findings about (S)-Azetidine-2-carboxylic acid,belong chiral-catalyst compound

Reference£º
Patent; SAINT LOUIS UNIVERSITY; WASHINGTON UNIVERSITY; RUMINSKI, Peter, G.; MEYERS, Marvin, L.; HEIER, Richard, F.; RETTIG, Michael, P.; DIPERSIO, John; (139 pag.)WO2018/85552; (2018); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare

Name is (S)-Azetidine-2-carboxylic acid, as a common heterocyclic compound, it belongs to chiral-catalyst compound, and cas is 2133-34-8, its synthesis route is as follows.,2133-34-8

EXAMPLE 3 Methanol (40mL) was added to the (R)-4-phthalimido-2-chlorobutyric acid (5 g) and the mixture was stirred. To the mixture 80% hydrazine hydrate (2.3 g) was added with stirring, and the mixture was stirred at 40C overnight. Water (30 mL) was then added to the mixture with stirring, and 47% sulfuric acid (13 mL) was added. The mixture was stirred at room temperature for 4 hours and the precipitate was filtered out. The filtrate was concentrated under reduced pressure to recover an aqueous solution of (R)-4-amino-2-chlorobutyric acid. A small amount of the solution was sampled to identify the molecular structure by NMR. The analytical data was as follows:1H-NMR (D2O): delta 2.15-2.45 (m,2H), 3.19 (t,2H), 4.45 (t, 1H) The solution was then placed in an ice bath and an aqueous sodium hydroxide solution (400 g/L) was added to the solution in order to adjust the pH of the solution to 2.0. Water was added to the solution to obtain about 130 g of solution. The resultant solution was heated to about 90C with stirring. Magnesium hydroxide (1.0 g) was added to the solution and the solution was stirred for 5 hours to produce an aqueous solution of (S)-azetidine-2-carboxylic acid. A small amount of the solution was sampled to identify the molecular structure by NMR. The analytical data was as follows: 1H-NMR (CD3OD): delta 2.15 (m,1H), 2.58 (m,1H), 3.90 (m,1H), 4.02 (q,1H), 4.60 (t,1H) The solution was spontaneously cooled to room temperature. Sodium carbonate (2.1 g) and DIBOC (4.3 g) were added with stirring and the mixture was further stirred overnight. Hydrochloric acid (6N) was added to the solution in order to adjust the pH of the solution to 2.0. The resultant solution was extracted with ethyl acetate three times. The resultant organic solution was washed with a saturated brine solution and dried with sodium sulfate. The solvent in the mixture was then removed to recover (S)-N-(tert-butoxycarbonyl)azetidine-2-carboxylic acid (2.1 g) (yield 55%, optical purity 89.3 %e.e.). A small amount of the solution was sampled to identify the molecular structure by NMR. The analytical data was as follows:1H-NMR (CDCl3): delta 1.48 (s,9H), 2.40-2.60 (bs,2H), 3.80-4.00 (bs,2H), 4.80 (t,1H)

With the complex challenges of chemical substances, we look forward to future research findings about (S)-Azetidine-2-carboxylic acid

Reference£º
Patent; KANEKA CORPORATION; EP1415985; (2004); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare

Name is (S)-Azetidine-2-carboxylic acid, as a common heterocyclic compound, it belongs to chiral-catalyst compound, and cas is 2133-34-8, its synthesis route is as follows.,2133-34-8

EXAMPLE 4 Dioxane (3 mL) was added to (S)-4-phthalimido-2-hydroxybutyric acid (1.0 g) in a nitrogen atmosphere. Thionyl chloride (2.5 g) was added to the mixture with stirring, and the mixture was stirred at 40C for one hour. Pyridine (0.06 g) was then added to the mixture and further stirred at 40C for 15 hours to produce a solution of dioxane and (R)-4-phthalimido-2-chlorobutyryl chloride. The solution was placed in an ice bath and then water (5 mL) was added with stirring. The solution was extracted with ethyl acetate at room temperature. The resultant organic solution was washed with a brine solution and was dried with mirabilite. The resultant solution containing ethyl acetate was concentrated under reduced pressure to recover (R)-4-phthalimido-2-chlorobutyric acid. Methanol (9 mL) was added to the compound. To the mixture 80% hydrazine hydrate (0.5 g) was added with stirring, and the mixture was stirred at 40C overnight. Water (6 mL) was then added to the solution with stirring and 47% sulfuric acid (3 mL) was added to the solution. The mixture was stirred at room temperature for three hours and the precipitate was filtered. The filtrate was concentrated under reduced pressure to produce an aqueous solution of (R)-4-amino-2-chlorobutyric acid. The solution was then placed in an ice bath and an aqueous sodium hydroxide solution (400 g/L) was added to the solution in order to adjust the pH of the solution to 2.0. Water was added to the solution to obtain about 30 g of solution. The resultant solution was heated to about 80C with stirring. Magnesium hydroxide (0.20 g) was added to the solution and the solution was stirred for 10 hours to produce an aqueous solution of (S)-azetidine-2-carboxylic acid. The solution was spontaneously cooled to room temperature. Sodium carbonate (0.43 g) and DIBOC (0.90 g) were added with stirring and the mixture was further stirred overnight. Hydrochloric acid (6N) was added to the solution in order to adjust the pH of the solution to 2.0. The resultant mixture was extracted with ethyl acetate three times. The resultant organic solution was washed with a saturated brine solution and dried with sodium sulfate. The solvent in the mixture was then removed to recover (S)-N-(tert-butoxycarbonyl)azetidine-2-carboxylic acid (0.32 g) (yield 41%, optical purity 87.1 %e.e.).

With the complex challenges of chemical substances, we look forward to future research findings about (S)-Azetidine-2-carboxylic acid

Reference£º
Patent; KANEKA CORPORATION; EP1415985; (2004); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare

As a common heterocyclic compound, it belong chiral-catalyst compound,(S)-Azetidine-2-carboxylic acid,2133-34-8,Molecular formula: C4H7NO2,mainly used in chemical industry, its synthesis route is as follows.,2133-34-8

Synthesis of Azethidine-2-carboxylic Acid N-carboxyamino Acid Anhydride At room temperature, (S)-azethidine-2-carboxylic acid (1.0 g, 99.9% ee or higher) was suspended in 25 ml of tetrahydrofuran. Then tri-phosgene (1.0 g) was added thereto. The suspension was heated to 50 C. and stirred for 4 hours. After allowing to cool, the solvent was distilled off under reduced pressure to give a pale yellow oil (1.5 g). 1H-NMR(CDC13) delta 4.52 (dd, 1H), 3.76-3.62 (m, 2H), 2.44-2.36 (m, 1H), 2.23-2.14 (m, 1H), 13C-NMR (CDC13) delta 169.10, 152.27, 55.44, 40.37, 34.22.

With the synthetic route has been constantly updated, we look forward to future research findings about (S)-Azetidine-2-carboxylic acid,belong chiral-catalyst compound

Reference£º
Patent; Matsuo, Kazuhiko; Tsukuya, Kentaro; US2002/151721; (2002); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2133-34-8,(S)-Azetidine-2-carboxylic acid,as a common compound, the synthetic route is as follows.

Step A. N-(3,5-Dichlorobenzenesulfonyl)-2(S)-azetidinecarboxylic Acid To a magnetically stirred mixture of azetidine-2(S)-carboxylic acid (1 g, 10.5 mmol) and Na2CO3 (2.76 g, 20 mmol) in 15 mL of water at 0 C. was added 3.5-dichlorobenzenesulfonyl chloride (2.94 g, 12 mmol), and the reaction was allowed to slowly warm up to room temperature overnight. The reaction was quenched by careful addition of concentrated HCl at 0 C. (pH=ca. 2), and the product was extracted with EtOAc (3*15 mL). The extracts were dried over Na2SO4, and concentrated to dryness to provide the final productproduct as a white solid, which is >90% pure by 1H NMR and was used directly. 500 MHz 1H NMR (CD3OD): delta 2.3-2.4 (m, 2H), 3.39 (m, 1H), 3.95 (q, J=9 Hz, 1H), 4.68 (t, 1H, J=8.5 Hz), 7.62 (t, 1H, J=8 Hz), 7.73-7.70 (m, 1H), 7.79 (t, J=2 Hz, 1H), 7.84 (d, J=2 Hz, 1H)., 2133-34-8

2133-34-8 (S)-Azetidine-2-carboxylic acid 16486, achiral-catalyst compound, is more and more widely used in various fields.

Reference£º
Patent; Merck & Co., Inc.; US6645939; (2003); B1;,
Chiral Catalysts
Chiral catalysts – SlideShare

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2133-34-8,(S)-Azetidine-2-carboxylic acid,as a common compound, the synthetic route is as follows.

Step A. N-(2-Thiophene-sulfonyl)-azetidine-2(S)-carboxylic Acid To a magnetically stirred mixture of azetidine-2(S)-carboxylic acid (1.0 g, 10 mmol) and Na2CO3 (2.1 g, 20 mmol) in 30 mL of water at 0 C. was added thiophene-2-sulfonyl chloride (1.8 g, 10 mmol), and the reaction was allowed to slowly warm up to room temperature overnight. The reaction was quenched by careful addition of concentrated HCl at 0 C. to pH above 2, and the product was extracted with EtOAc (3*15 mL). The extracts were dried over Na2SO4, and concentrated to dryness to provide the title compound as a white solid, which is >90% pure by 1H-NMR and used without further purification. 400 MHz 1H NMR (CD3OD): delta 2.2-2.4 (m, 2H), 3.7-3.9 (m, 2H), 4.42 (dd, 1H), 7.30 (dd, 1H), 7.75 (dd, 1H), 7.95 (dd, 1H)., 2133-34-8

As the paragraph descriping shows that 2133-34-8 is playing an increasingly important role.

Reference£º
Patent; Merck & Co., Inc.; US6645939; (2003); B1;,
Chiral Catalysts
Chiral catalysts – SlideShare