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CAS No. : | 1214741-19-1 | MDL No. : | MFCD20488025 |
Formula : | C11H15NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PBHXYYXEZQXDLB-LDYMZIIASA-N |
M.W : | 225.24 | Pubchem ID : | 77174616 |
Synonyms : |
|
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.73 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 59.04 |
TPSA : | 63.68 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) : | -7.01 cm/s |
Log Po/w (iLOGP) : | 1.44 |
Log Po/w (XLOGP3) : | 0.93 |
Log Po/w (WLOGP) : | 0.09 |
Log Po/w (MLOGP) : | 0.53 |
Log Po/w (SILICOS-IT) : | 1.09 |
Consensus Log Po/w : | 0.82 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.69 |
Solubility : | 4.59 mg/ml ; 0.0204 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.85 |
Solubility : | 3.16 mg/ml ; 0.014 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.32 |
Solubility : | 10.8 mg/ml ; 0.048 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.33 |
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 |
---|---|---|
61% | Stage #1: With 1,3-dimethyl-2-imidazolidinone; chloro-trimethyl-silane; copper(l) chloride; lithium hexamethyldisilazane In tetrahydrofuran at -60 - 10℃; for 0.5 h; Inert atmosphere Stage #2: With trifluoroacetic acid In water at 5 - 25℃; for 3.66667 h; |
To a 2 L three neck flask equipped with an agitator, thermometer, reflux condenser, and a nitrogen inlet were charged XIV (100 g, 0.5 mol), CuCl (10 g), DMI (100 mL), THF (1.2 L), and methyl formate (100 mL). After cooling to below [−60]° C., LHMDS (700 mL, 1.0 M in THF) was charged at a rate such that the temperature did not exceed −60° C. After addition of LHMDS, TMSCl was charged at a rate such that the temperature did not exceed [−60]° C. The mixture was warmed to between 0 and 10° C. over 30 min and the batch was concentrated in vacuum to 250 mL and EtOAc (300 mL) was added. To a mixture of citric acid (120 g), water (1 L), and EtOAc (1 L) at 5° C. was then transferred the crude reaction mixture over 30 min while maintaining a temperature between 0 and 15° C. The flask containing the crude mixture was then rinsed with EtOAc (200 mL). After agitating for 10 min, the layers were separated and the organic layer was sequentially washed with 12.5percent aq. citric acid (800 mL), 10percent aq. citric acid (700 mL) and 8percent aq. citric acid solution (600 mL). To a mixture of the organic layer and water (300 mL) at 5° C., was charged trifluoroacetic acid (30 mL) over 10 min while maintaining a temperature between 5 and 15° C. After completing the addition, the mixture was warmed to 25° C. and agitated for 3.5 h. An aqueous solution of KHCO3 (200 mL, 20percent) was charged over 30 min while maintaining a temperature below 20° C., followed by saturated NaCl solution (500 mL) and the layers were separated and split. The aqueous layer was back extracted with EtOAc (250 mL). The EtOAc fraction was washed with saturated NaCl solution (500 mL). Water (35 mL) was charged to the combined organic layers and the solution was concentrated in vacuum to a final volume of 100 mL. MTBE (400 mL) was charged and the mixture was concentrated in vacuum to a final volume of 100 mL. Additional MTBE (400 mL) was charged and the suspension was agitated for 2 h at RT. The resulting slurry was filtered, rinsed with MTBE (200 mL) and XV was obtained in 61percent yield (70 g) after drying in vacuum at 45° C. for 12 h. MP 196° C.-198° C. 1H NMR (400 MHz in CDCl3): δ 9.7 (s, 1H), 5.5 (s, 1H), 2.7 (m, 1H), 2.6 (m, 1H), 2.4 (m, 2H), 0.9 (s, 9H). 13CNMR (400 MHz, CDCl3): 192.0, 181.1, 169.7, 97.6, 73.4, 36.5, 31.7, 30.6, 24.6. ES-MS: [M+H+]calcd for C11H15NO4: 226.10. found: 226.27. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | Stage #1: With sodium hexamethyldisilazane In toluene at 10℃; for 1 h; Stage #2: at 10℃; |
To a 3-neck 1-L flask equipped with a thermometer and mechanical stirrer were charged Ph3PCH3Br (122.9 g; 344.1 mmol) and toluene (100 mL). At 10° C., a solution of NaHMDS in toluene (540 mL, 13percent) was added slowly to maintain the temperature at 10° C. This slurry was agitated at 10° C. for 1 h and then added slowly to a slurry of XV (50 g, 222 mmol) in toluene (100 mL) at 10° C., over a period of 2-4 h via peristaltic pump. After stirring for an additional hour, the batch was quenched into a solution of NaCl (10percent aqueous), AcOH (38.5 mL, 666 mmol), and toluene (50 mL) over 30 min at 25° C. The resulting mixture was stirred for 30 min and the layers were settled, split and the lower aqueous layer was removed. The organic layer was then treated with MgCl2 powder (70 g, 776 mmol) for 2 h at RT. The solids were then filtered off and the solid MgCl2-triphenylphosphin oxide complex was washed with MTBE (100 mL). The organic filtrates were combined, washed with aq. NaCl (100 mL, 10percent) and concentrated to 100 mL in vacuum. To the resulting slurry was charged heptane (400 mL) and the volume was reduced to 100 mL in vacuum. Additional heptane (400 mL) was added and the volume was reduced to 250 mL in vacuum. A third portion of heptane (400 mL) was added; the batch was then cooled to 0° C. over 2 h and stirred for another 2 h at this temperature. The solids were then removed by filtration and washed with ice-cold N-heptane (200 mL). The wet cake was dried under vacuum at 30° C. for 18 h to produce 62 g of XVI (63percent yield) as an off-white solid. Mp 85° C.-87° C. 1H-NMR (CDCl3) δ 5.98 (m, 1H), 5.31 (m, 3H), 2.56 (m, 1H), 2.17 (m, 3H), 0.81 (s, 9H). ES-MS: [M+H+]calcd for C12H18NO3: 224.12. found: 224.38. |
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