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CAS No. : | 1315020-11-1 | MDL No. : | MFCD08234637 |
Formula : | C5H9NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NOGODPXRSZBASZ-SCSAIBSYSA-N |
M.W : | 131.13 | Pubchem ID : | 55252549 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.8 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 33.68 |
TPSA : | 49.77 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) : | -7.61 cm/s |
Log Po/w (iLOGP) : | 1.03 |
Log Po/w (XLOGP3) : | -0.72 |
Log Po/w (WLOGP) : | -0.95 |
Log Po/w (MLOGP) : | -0.82 |
Log Po/w (SILICOS-IT) : | -0.32 |
Consensus Log Po/w : | -0.36 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.13 |
Solubility : | 96.4 mg/ml ; 0.736 mol/l |
Class : | Very soluble |
Log S (Ali) : | 0.15 |
Solubility : | 186.0 mg/ml ; 1.42 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | 0.37 |
Solubility : | 310.0 mg/ml ; 2.37 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.29 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362 | UN#: | N/A |
Hazard Statements: | H315-H319 | 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 |
---|---|---|
94% | Stage #1: (5R)-5-(hydroxymethyl)-3-methyl-1,3-oxazolidin-2-one With trimethylamine hydrochloride; triethylamine In dichloromethane at 0℃; for 0.166667h; Stage #2: p-toluenesulfonyl chloride In dichloromethane at 20℃; | 6DA [(5R)-3-methyl-2-oxo-1,3-oxazolidin-5-yl]methyl 4-methylbenzenesulfonate A mixture of Intermediate 159 (2.74 g, 20.9 mmo[), TEA (4.4 mL, 31 mmo[) andtrimethy[amine hydroch[oride (200 mg, 2.09 mmo[) in DCM (61 mL) was coo[ed to0°C and stirred for 10 minutes. 4-Methy[benzenesu[fony[ ch[oride (4.38 g, 23.0mmo[) was added in 3 portions and the so[ution stirred at RT unti[ comp[ete conversion. The reaction mixture was treated with N,N-dimethy[ethy[enediamine (2.7 mL, 25 mmo[) to consume unreacted 4-methy[benzenesu[fony[ ch[oride. Water was added, the aqueous phase extracted with DCM (three times) and the combined organic [ayers concentrated to dryness to give 5.97 g (94% yie[d) of the tit[ecompound, which was used without further purification.1H NMR (400 MHz, DMSO-d6): ö ppm 2.43 (5, 3 H) 2.66 - 2.73 (m, 3 H) 3.17 (dd, 1 H)3.57 (t, 1 H) 4.09 - 4.17 (m, 1 H) 4.18 - 4.25 (m, 1 H) 4.69 (dt, 1 H) 7.47 - 7.55 (m,2 H) 7.75 - 7.85 (m, 2 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27% | With potassium <i>tert</i>-butylate at 100℃; for 24h; | 159 (5R)-5-(hydroxymethyl)-3-methyl-1,3-oxazolidin-2-one To a so[ution of Intermediate 158 (2.58 g, 24.5 mmo[) in diethy[ carbonate (18 mL, 150 mmo[) was added potassium tert-butoxide (138 mg, 1.23 mmo[). The reaction mixture was stirred for 24h at 100°C and evaporated to dryness. The residue was purified by co[umn chromatography (si[ica ge[, EtOAc/ hexane gradient) to give 861mg (27% yie[d) of the tit[e compound.1H NMR (400 MHz, DMSO-d6): ö [ppm] 2.72 (5, 3 H) 3.27 (dd, 1 H) 3.47 (dd, 1 H) 3.49- 3.58 (m, 2 H) 4.40 - 4.51 (m, 1 H) 5.10 (t, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: triethylamine; trimethylamine hydrochloride / dichloromethane / 0.17 h / 0 °C 1.2: 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: triethylamine; trimethylamine hydrochloride / dichloromethane / 0.17 h / 0 °C 1.2: 20 °C 2.1: caesium carbonate / N,N-dimethyl-formamide / 90 °C 3.1: sodium hydroxide / methanol; water; tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | With pyridine; thionyl chloride In 1,2-dichloro-ethane at 90℃; for 1h; | Intermediate 18: (R)-5-(chloromethyl)-3-methyloxazolidin-2-one. To (R)-5-(hydroxymethyl)-3-methyloxazolidin-2-one (518.2 mg, 3.952 mmol) stirring in DCE (20 mL) in a round bottom flask at rt was added SOCL (1.5 mL, 20.677 mmol) followed by pyridine (1.6 mL, 19.863 mmol). The reaction was connected to a reflux apparatus and stirred at 90 °C for 1 h. The reaction mixture was then cooled to rt, then cooled to 0 °C and quenched by the dropwise addition of a saturated aqueous solution of NaHCCb until pH 7 was reached. The layers were separated and the organic layer was washed with saturated aqueous solutions of NaHCCb (x 3), MLCl (x 3), then CuSCb (x 2). The organic layer was then dried (Na2SCb) and concentrated under reduced pressure to afford the title compound as a yellow oil (172.2 mg, 29%). NMR (500 MHz, CDCb) d 4.70 (dddd, J= 8.7, 7.0, 5.7, 4.1 Hz, 1H), 3.78 - 3.59 (m, 3H), 3.46 (dd, J= 9.0, 5.7 Hz, 1H), 2.90 (s, 3H). |
With pyridine; thionyl chloride In 1,2-dichloro-ethane at 90℃; for 1h; | Intermediate 18: (R)-5-(Chloromethyl)-3-methyloxazolidin-2-one To (R)-5-(hydroxymethyl)-3-methyloxazolidin-2-one (518.2 mg, 3.952 mmol) stirring in DCE (20 mL) in a round bottom flask at rt was added SOCl2 (1.5 mL, 20.677 mmol) followed by pyridine (1.6 mL, 19.863 mmol). The reaction was connected to a reflux apparatus and stirred at 90° C. for 1 h. The reaction mixture was then cooled to rt, then cooled to 0° C. and quenched by the dropwise addition of a saturated aqueous solution of NaHCO3 until pH 7 was reached. The layers were separated and the organic layer was washed with saturated aqueous solutions of NaHCO3 (*3), NH4C1 (*3), then CuSO4 (*2). The organic layer was then dried (Na2SO4) and concentrated under reduced pressure to afford the title compound as a yellow oil (172.2 mg, 29%). 1H NMR (500 MHz, CDCl3) δ 4.70 (dddd, J=8.7, 7.0, 5.7, 4.1 Hz, 1H), 3.78-3.59 (m, 3H), 3.46 (dd, J=9.0, 5.7 Hz, 1H), 2.90 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: thionyl chloride; pyridine / 1,2-dichloro-ethane / 1 h / 90 °C 2: caesium carbonate / N,N-dimethyl-formamide / 20 h / 20 °C | ||
Multi-step reaction with 2 steps 1: thionyl chloride; pyridine / 1,2-dichloro-ethane / 1 h / 90 °C 2: caesium carbonate / N,N-dimethyl-formamide / 20 h / 20 °C |
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