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CAS No. : | 2133-34-8 | MDL No. : | MFCD00005166 |
Formula : | C4H7NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 101.10 | Pubchem ID : | - |
Synonyms : |
L-Azetidine-2-carboxylic acid;A2C;(S)-(–)-Azetidine-2-carboxylic Acid;LACA;L-AZC;Aze
|
Num. heavy atoms : | 7 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.75 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 27.72 |
TPSA : | 49.33 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -8.93 cm/s |
Log Po/w (iLOGP) : | 0.86 |
Log Po/w (XLOGP3) : | -2.84 |
Log Po/w (WLOGP) : | -0.95 |
Log Po/w (MLOGP) : | -3.0 |
Log Po/w (SILICOS-IT) : | -0.02 |
Consensus Log Po/w : | -1.19 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 3.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | 1.39 |
Solubility : | 2470.0 mg/ml ; 24.5 mol/l |
Class : | Highly soluble |
Log S (Ali) : | 2.36 |
Solubility : | 23200.0 mg/ml ; 229.0 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | 0.17 |
Solubility : | 150.0 mg/ml ; 1.49 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.37 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Stage #1: With sodium hydroxide; water In ethanol at 0 - 20℃; Stage #2: With hydrogenchloride In water |
Example 15 (S)-1-(tert-Butoxycarbonyl)azetidine-2-carboxylic Acid (13). To a solution of (S)-2-azetidinecarboxylic acid 12 (1.0 g, 10.0 mmol) and di-tert-butyl dicarbonate (2.83 g, 12.5 mmol) in ethanol (20 mL) and water (10 mL) was added NaOH (420 mg, 10.5 mmol) at 0° C. The mixture was stirred overnight at ambient temperature. After evaporation of the ethanol, water (20 mL) was added, then acidified with diluted HCl to a pH of 3 and extracted with ethyl acetate (50 mL*3). The combined ethyl acetate was washed with water (30 mL) and saturated NaCl (30 mL), and dried over Na2 SO4. After evaporation of the ethyl acetate to afford 1.98 g (100percent) of 13 as a white solid. 1H NMR (300 MHz, CDCl3) δ 4.79 (m, 1H), 3.93 (m, 2H), 2.46 (m, 2H), 1.48 (s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | Stage #1: for 12 h; |
EXAMPLE 3 Methanol (40mL) was added to the (R)-4-phthalimido-2-chlorobutyric acid (5 g) and the mixture was stirred. To the mixture 80percent hydrazine hydrate (2.3 g) was added with stirring, and the mixture was stirred at 40°C overnight. Water (30 mL) was then added to the mixture with stirring, and 47percent 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): δ 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 90°C 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): δ 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.(TM). (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 55percent, optical purity 89.3 percente.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): δ 1.48 (s,9H), 2.40-2.60 (bs,2H), 3.80-4.00 (bs,2H), 4.80 (t,1H) |
41% | Stage #1: for 12 h; |
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 40°C for one hour. Pyridine (0.06 g) was then added to the mixture and further stirred at 40°C 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 80percent hydrazine hydrate (0.5 g) was added with stirring, and the mixture was stirred at 40°C overnight. Water (6 mL) was then added to the solution with stirring and 47percent 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 80°C 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.(TM). (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 41percent, optical purity 87.1 percente.e.). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63.1% | Stage #1: With 4-methyl-morpholine In 1,4-dioxane; water at 0 - 25℃; for 22 h; Stage #2: With hydrogenchloride In water at 0℃; |
A mixture of (S)-2-azetidinecarboxyic acid (1Og, 98.9mmol), di-tert butyl dicarbonate (28.06g, 128.6mmol), N-methyl morpholine (11.5g, 113.7mmol), 1,4-dioxane (160ml) and water (160ml) was stirred at O0C for 4 hours and then at ambient temperature for 18 hours. The volatiles were removed by evaporation and the residue was dissolved in water, washed with DCM and the aqueous layer acidified to pH 1.0 at O0C with concentrated hydrochloric acid. The aqueous layer was extracted with DCM and the organic layer dried (Na2SO4) over anhydrous sodium sulfate to give iV-tert-butyloxycarbonylazetidin-2-yl carboxylic acid (12.61g, 63.1percent) as an oil; NMR Spectrum (CDCl3) 1.42 (s, 9H), 2.40 (m, IH), 2.59 (m, IH), 3.90 (m, 2H), 4.80 (t, IH). |
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