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CAS No. : | 59830-60-3 | MDL No. : | MFCD00798796 |
Formula : | C17H17NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HZDPJHOWPIVWMR-INIZCTEOSA-N |
M.W : | 283.32 | Pubchem ID : | 7021150 |
Synonyms : |
|
Num. heavy atoms : | 21 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.18 |
Num. rotatable bonds : | 8 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 79.8 |
TPSA : | 55.4 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.93 cm/s |
Log Po/w (iLOGP) : | 2.52 |
Log Po/w (XLOGP3) : | 2.96 |
Log Po/w (WLOGP) : | 2.57 |
Log Po/w (MLOGP) : | 2.49 |
Log Po/w (SILICOS-IT) : | 3.14 |
Consensus Log Po/w : | 2.74 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.36 |
Solubility : | 0.125 mg/ml ; 0.00044 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.79 |
Solubility : | 0.0464 mg/ml ; 0.000164 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -5.46 |
Solubility : | 0.000987 mg/ml ; 0.00000348 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.77 |
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 lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 2 h; Stage #2: With hydrogenchloride; water In tetrahydrofuran |
Lithium aluminum hydride (0.95 mL of a 1.0 M solution in THF, 0.95 mmoles) was added to a room temperature solution of [(S)-1-(Methoxy-methyl-carbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester (0.30 g, 0.86 mmoles) in THF (10 mL). The resulting mixture was stirred at room temperature for 2 h, then was quenched by dilution with EtOAc (200 mL), and washed with 1percent aqueous HCl (200 mL). The organic layer was dried (MgSO4) and concentrated in vacuo. The residue was repeatedly diluted with CH3CN (2.x.200 mL) and concentrated in vacuo to give 0.24 g (approximately quantitative yield) of ((S)-1-Benzyl-2-oxo-ethyl)-carbamic acid benzyl ester as a colorless oil, which was carried on without further purification: ES+LC/MS m/e 284 (M+H), RT=4.75 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With sulfur trioxide pyridine complex; N-ethyl-N,N-diisopropylamine In dichloromethane; dimethyl sulfoxide at 0℃; for 0.5 h; | Reference compound 7 (40 g, 140 mmol) was dissolved in dimethyl sulfoxide (160 mL) and dichloromethane (80 mL) and the mixture was ice-cooled. Thereto was added a suspension (80 mL) of N,N-diisopropylethylamine (54 g, 420 mmol) and sulfur trioxide pyridine complex (67 g, 420 mmol) in dimethyl sulfoxide. This solution was stirred under ice-cooling for 30 min. This reaction mixture was diluted with ethyl acetate, washed with 1M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was crystallized from a hexane/ethyl acetate mixed solution to give Reference compound 25 (30 g, 76percent) as colorless crystals. mp 66.2-66.9°C. 1H-NMR (300 MHz, DMSO-d6)δ:2.72 (dd, 1H, J = 14.1, 10.4 Hz), 3.15 (dd, 1H, J = 14.1, 4.2 Hz), 4.2 (m, 1H), 4.96-5.05 (m, 2H), 7.19-7.39 (m, 10H), 7.76 (d, 1H, J = 7.8 Hz), 9.57 (s, 1H). Anal. Calcd for C17H17NO3: C, 72.07; H, 6.05; N, 4.94. Found: C, 71.69; H, 6.30; N, 4.76. |
1.1 g | With Dess-Martin periodane In dichloromethane at 0 - 20℃; Inert atmosphere | Intermediate S20 (0.250 g, 0.86 mmol) and Dess-Martin periodinane (1.53 g, 3.62 mmol) in DCM (50 mL) was stirred at 0 °C and then allowed to warm room temperature. The additional amount of oxidant was added if the conversion was not complete (TLC control, light petroleum ether : EtOAc, 1:1). After completion of the reaction, it was diluted with DCM (20 mL). The reaction mixture was washed with 0.2 M Na2S2O3 solution (2 x 20 mL) then with 1 M NaHCO3 solution (2x20 mL) and brine (20 mL). The organic phase was dried over Na2SO4 and evaporated in vacuo. Crude product was purified by flash chromatography eluting with a mixture of light petroleum ether : EtOAc, 1:1 to provide 31a (0.10 g, 40percent) as colourless solid. |
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