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CAS No. : | 159749-28-7 | MDL No. : | MFCD01861756 |
Formula : | C9H15NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 201.22 | Pubchem ID : | - |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.78 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 53.56 |
TPSA : | 66.84 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) : | -6.91 cm/s |
Log Po/w (iLOGP) : | 2.07 |
Log Po/w (XLOGP3) : | 0.87 |
Log Po/w (WLOGP) : | 0.7 |
Log Po/w (MLOGP) : | 0.43 |
Log Po/w (SILICOS-IT) : | -0.06 |
Consensus Log Po/w : | 0.8 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -1.37 |
Solubility : | 8.55 mg/ml ; 0.0425 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.86 |
Solubility : | 2.79 mg/ml ; 0.0139 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.1 |
Solubility : | 162.0 mg/ml ; 0.804 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.59 |
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 |
---|---|---|
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). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.5 g | Stage #1: With hydrogen; palladium(II) hydroxide In methanol at 50℃; for 7 h; Stage #2: With sodium hydroxide In methanol at 20℃; Stage #3: With hydrogenchloride In methanol; water |
A mixture of 12a (3.70 g, 13.2 mmol), Di-tert butyl dicarbonate (5.70 g, 26.3 mmol), and Pd(OH)2 (0.90 g, 6.43 mmol) in MeOH (100 mL) was stirred under H2 atmosphere at 50°C for 7 hours. The reaction mixture was cooled to room temperature and filtered. The filtrate was treated with 2 N NaOH (40 mL) and stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure. The residue was extracted with EtOAc (50 mL). The liquid phase was acified with 1 N HC1, adjusted pH=2 and extracted with DCM:i- PrOH = 4: 1 (150 mL x 3). The combined organic layers was washed with water (100 mL), dried over Na2S04 and concentrated under reduced pressure to give the title compound 12b (2.50 g) as colorless oil. MS-ESI (m/z): 146.0 [M + 1 - 56]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | Stage #1: With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -10 - 25℃; for 4 h; Stage #2: at 18 - 25℃; for 18 h; |
Isobutyl chloroformate (8.43 Ig, 61.7mmol) was added to a solution of iV-tert- butyloxycarbonylazetidin-2-yl carboxylic acid (12.42g, 61.7mmol) and N-methyl morpholine (6.23g, 61.7mmol) in anhydrous THF (20ml) cooled at -10°C under an nitrogen atmosphere, at such a rate to keep the reaction temperature below -8 0C. The reaction mixture was then stirred at -8 °C for 1 hour and then at ambient temperature for a further 3 hours. Methanol (200ml) was added and the reaction mixture stirred at ambient temperature for 18 hours. The volatiles were removed by evaporation and the residue partitioned between water and diethylether. The organic layer was separated, dried (Na2SO4) give methyl N-tert- butyloxycarbonylazetidin-2-yl carboxylate (11.15g, 84.0percent) as an oil; NMR Spectrum (CDCl3) 1.43 (s, 9H), 2.20 (m, IH), 2.50 (m, IH), 3.78 (s, 3H), 3.90 (m, IH), 4.00 (m, IH), 4.60 (m, IH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.25 g | With dimethylsulfide borane complex In tetrahydrofuran at 0 - 20℃; for 3 h; | To a solution of 12b (1.45 g, 7.21 mmol) in anhydrous THF (12 mL) was added dropwise Borane-methyl sulfide complex (10M, 3 mL) at 0 °C. The reaction mixture was warmed to room temperature for 3 hours. Then it was quenched with MeOH (10 mL), diluted with DCM (100 mL), washed with water (40 mL χ 3), dried over Na2S04 and concentrated under reduced pressure to give the title compound 12c (1.25 g) as colorless oil. MS-ESI (m/z): 132.0 [M + 1 - 56]+. |
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