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CAS No. : | 118994-89-1 | MDL No. : | MFCD04114930 |
Formula : | C6H7NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KRMORCCAHXFIHF-UHFFFAOYSA-N |
M.W : | 141.12 | Pubchem ID : | 10964603 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.33 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 32.59 |
TPSA : | 52.33 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.53 cm/s |
Log Po/w (iLOGP) : | 1.76 |
Log Po/w (XLOGP3) : | 0.89 |
Log Po/w (WLOGP) : | 0.85 |
Log Po/w (MLOGP) : | -0.43 |
Log Po/w (SILICOS-IT) : | 0.94 |
Consensus Log Po/w : | 0.8 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.45 |
Solubility : | 5.03 mg/ml ; 0.0357 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.57 |
Solubility : | 3.77 mg/ml ; 0.0267 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.69 |
Solubility : | 2.86 mg/ml ; 0.0203 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.09 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
86% | With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 0.5 h; | A solution of 33 (29.13 g, 0.207 mol) in THF (206 mL) was added dropwise to a suspension of LiAlH4 (7.85 g, 0.207 mmol) in THF (206 mL) at 0 °C. The reaction mixture was stirred for 30 min at 0 °C (at this point TLC indicated consumption of the SM) and quenched by successive addition of water (8 mL), 10percent NaOH (8 mL) solution, and water (24 mL). The temperature should not exceed 0 °C). The precipitate was filtered and washed several times with THF. The filtrate was evaporated to give 34, which was used without purification. M = 17.7 g. Yield = 86percent. |
70% | With sodium tetrahydroborate In ethanol at 0 - 20℃; | Example A.8 Ethyl oxazole-5-carboxylate (1 g, 7.09 mmol, 1 eq) was dissolved in EtOH(l4mL) and the mixture was cooled to 0°C. Sodium borohydride (0.54 g, 14.1 7mmol, 2eq) was added portionwise while stirring, and then the mixture was allowed to warm to r.t.. After overnight stirring at r.t. the conversion was complete by TLC (95/5 DCM/MeOH). The mixture was cooled to 0°C and 2N HC1 was added dropwise till gas evolution ceased (pH 5-6). The obtained suspension was concentrated at reducedpressure, and the residue was purified by flash chromatography (5i02) using as eluent a mixture DCM/MeOH = 95/5. The pure intermediate (11) were obtained as colourless oil (0.49 g, yield 70percent). |
58% | With sodium tetrahydroborate In ethanol at 0 - 20℃; for 16 h; Inert atmosphere | [000282] Synthesis of oxazol-5-ylmethanol (343): To a stirred solution of ethyl oxazole-5- carboxylate 342 (2 g, 14.18 mmol) in EtOH (20 mL) under argon atmosphere was added sodium borohydride (1.07 g, 28.36 mmol) at 0 °C; warmed to RT and stirred for 16 h. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was quenched with saturated ammonium chloride solution (25 mL) and extracted with 5percent MeOH/ CH2C12 (2 x 20 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to obtain the crude. The crude was purified through silica gel column chromatography using 5percent MeOH/ CH2C12 to afford compound 343 (810 mg, 58percent) as colorless syrup. TLC: 5percent MeOH/ CH2C12 (R 0.3); 1H-NMR (DMSO-d6, 500 MHz): ö 8.28 (s, 1H), 7.04 (s, 1H), 5.36 (t, J 6.0 Hz, 1H), 4.47 (d, J 6.0 Hz, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane; toluene at 0 - 20℃; for 3 h; | INTERMEDIATE 171 - PREPARATION OF ethyl oxazole-5-carboxylate; 1 ,8-Diazabicyclo[5.4.0]undec-7-ene (0.574 ml 3.84 mmol) was added simultaneously with ethyl glyoxalate (50percent in toluene, 0.659 ml 3.33 mmol) to a mixture of tosylmethyl isocyanide (0.500 g; 2.560 mmol) in dichloromethane (10 ml.) at 00C. The resulting mixture was stirred at room temperature for 3 hours, diluted in dichloromethane and washed with sodium hydrogen sulphate, sodium carbonate, dried over magnesium sulphate and concentrated under reduced pressure. The crude mixture was purified by flash chromatography on silica (eluent 5 to 60 percent ethyl acetate in heptane) to yield 0.194 g (54 percent) of ethyl oxazole-5-carboxylate as a colorless oil.ESI/APCI(+): 142(M+H). |
51% | With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane; toluene at 0 - 20℃; for 8 h; | To a stirred solution of TosMIC (50.0 g, 256 mmol) in CH2Cl2 (255 mL) was added ethyl glyoxylate (~50percent in toluene, 56 mL, 283 mmol, 1.1 equiv). The solution was cooled to 0 °C, and at this temperature, DBU (38 mL, 254 mmol) was added dropwise. The reaction mixture was allowed to warm to ambient temperature and stirred for 8 h. The reaction mixture was washed with water (~300 mL), organic layers was dried over Na2SO4 and evaporated. The residue was distilled at reduced pressure. bp = 98 °C (25 mbar). M = 18.3 g. Yield = 51percent. 1H NMR: (CDCl3, 400 MHz) δ = 1.35 (t, J = 7.2 Hz, 3 H), 4.35 (q, J = 7.1 Hz, 2 H), 7.73 (s, 1 H), 7.99 (s, 1 H). 13C NMR (CDCl3, 100 MHz): δ = 14.2, 61.7, 133.3, 142.9, 153.3, 157.6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | Stage #1: With lithium hexamethyldisilazane In tetrahydrofuran at -60 - -50℃; for 1 h; Stage #2: With hexachloroethane In tetrahydrofuran at 25℃; for 12 h; |
To a solution of compound 6A (15.0 g, 106 mmol) in THF (150 mL) was added dropwise lithium hexamethyl disilazide (178 mL, 170 mmol) at -60 °C. The solution was stirred at -50 °C for 1 h. Then hexachloroethane (37,8 g, 160 mmol) was added to the solution. The solution was stirred at room temperature for 12 h. The reaction was quenched by saturated aq. NH4C1 solution (50 mL) and extracted with EtOAc (50 mL). The organic layer was separated, dried over Na2S04, concentrated under vacuum and the residue was purified with column chromatography to give compound 6B (10 g, 56percent) as colorless oil. 1H NMR (400 MHz, CDCI3) δ 7.71 (s, IH), 3.39 (q, J = 7.2 Hz, 2H), 1.38 (t, J = 7.2 Hz, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.5% | at 25℃; for 6.5 h; Large scale | An aqueous solution of lithium hydroxide monohydrate (124.5 kg of a solution preparedfrom 49.44 kg lithium hydroxide monohydrate dissolved in 319 kg water, 398 mol) was added to asolution of ethyl 5-oxazolecarboxylate (54 kg, 382.7 mol) in water (54 kg) maintaining the temperature below 25 °C. The reaction was stirred for 6.5 h and then conc. aqueous HCI (64.8 kg) was added maintaining the temperature below 25 °C, the crystallisation cooled to 5 °C and held forh. The product was filtered off, washed with cold water (88 kg), then isopropanol (171 kg) anddried under vacuum at 50 °C to give the title compound (37.88 kg, 87.Spercent).1H NMR (400 MHz, DMSO-d6) ppm 13.68 (br. 5., 1 H), 8.59 (5, 1 H), and 7.88 (5, 1 H). |
87.5% | With lithium hydroxide monohydrate In water at 25℃; for 6.5 h; Large scale | An aqueous solution of lithium hydroxide monohydrate (124.5 kg of a solution prepared from 49.44 kg lithium hydroxide monohydrate dissolved in 319 kg water, 398 mol) was added to a solution of ethyl 5-oxazolecarboxylate (54 kg, 382.7 mol) in water (54 kg) maintaining the temperature below 25 °C. The reaction was stirred for 6.5 h and then cone, aqueous HCI (64.8 kg) was added maintaining the temperature below 25 °C, the crystallisation cooled to 5 °C and held for 1 h. The product was filtered off, washed with cold water (88 kg), then isopropanol (171 kg) and dried under vacuum at 50 °C to give the title compound (37.88 kg, 87.5percent). (0437) *H NMR (400 MHz, DMSO-cfe) δ ppm 13.68 (br. s., 1 H), 8.59 (s, 1 H), and 7.88 (s, 1 H). |
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