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CAS No. : | 614-75-5 | MDL No. : | MFCD00004323 |
Formula : | C8H8O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CCVYRRGZDBSHFU-UHFFFAOYSA-N |
M.W : | 152.15 | Pubchem ID : | 11970 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 40.01 |
TPSA : | 57.53 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) : | -6.62 cm/s |
Log Po/w (iLOGP) : | 0.9 |
Log Po/w (XLOGP3) : | 0.85 |
Log Po/w (WLOGP) : | 1.02 |
Log Po/w (MLOGP) : | 1.05 |
Log Po/w (SILICOS-IT) : | 1.06 |
Consensus Log Po/w : | 0.98 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -1.59 |
Solubility : | 3.91 mg/ml ; 0.0257 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.64 |
Solubility : | 3.47 mg/ml ; 0.0228 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.58 |
Solubility : | 3.97 mg/ml ; 0.0261 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.18 |
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 |
---|---|---|
94% | With potassium carbonate In acetonitrile for 15 h; Heating / reflux | Example 9:; (2-Methoxy-phenyl) -acetic acid methyl ester; A solution of methyl iodide (188 g, 1.33 mole) in acetonitrile (200 mL) was slowly added to a mixture of (2-hydroxy-phenyl) -acetic acid (80 g, 0.53 mol) and potassium carbonate (254 g, 1.84 mol) in acetonitrile (800 mL) under reflux. The reaction was heated to reflux for 15 hours. The reaction mixture was cooled and the precipitate was removed by filtration. The filtrate was evaporated to dryness to give the crude product (90. g, 0.50 mol, 94 percent) |
89% | With potassium carbonate In acetone at 20℃; for 12 h; | To a stirred solution of 2-hydroxyphenylacetic acid (1.04 g, 6.8 mmol) in acetone (30 mL), K2CO3 (2.83 g, 20.5 mmol) and MeI (1.06 mL, 17.1 mmol) was added. The mixture was stirred at room temperature for 12 h and then acetone was removed at vacuum. Water (20 mL) was added to the mixture and extracted with ethyl acetate (2*30 mL). The organic layer was washed with water (2*20 mL), brine (20 mL), dried (Na2SO4) and concentrated. The crude product was purified by silica gel column chromatography to get 16 (1.10 g, 89percent) as colorless oil. Rf 0.5 (1:20 ethyl acetate:hexane); 1H NMR (CDCl3, 500 MHz) δ 7.24 (d, 1H, J=8.0Hz, C6′-H), 7.16 (d, 1H, J=8.0Hz, C3′-H), 6.92–6.85 (m, 2H, C4′-H & C5′-H), 3.80 (s, OCH3), 3.67 (s, 3H, CO2CH3), 3.62 (s, 2H, C2-H2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | at 20℃; for 2 h; | PREPARATION lA: methyl 2-(2-hydroxyphenyl)acetate: [0194] To a solution of 2-(2-hydroxyphenyl)acetic acid (400 g, 2.63 mmol) in MeOH (3.0 L) was bubbled with HCl (g) at room temperature for 2 hours. The resulting mixture was concentrated, dried under vacuo to give compound 1A (415 g, yield 95percent) as yellow oil, and the oil was solidified after standing overnight. [0195] JH NMR (CDCI3, 400 MHz): δ 7.20-7.16 (m, 1H), 7.11-7.09 (m, 1H), 6.93-6.86 (m, 2H), 4.48 (br s, 1H), 3.74 (s, 2H), 3.69 (s, 3H). |
90% | With hydrogenchloride In waterReflux | To a solution of compound 45 (2.0 g, 13.2mmol) in MeOH (30m1) was added HC1 solution (0.2 ml, 3 5percent), and the resulting mixture was heated under reflux overnight. Then themixture was concentrated, and the residue was dissolved in ethyl acetate (50 ml), and washed with NaHCO3, brine successively. The organic layer was dried over anhydrous Na2504, then filtered and concentrated, and the pale yellow solid was used for next step without further purification (yield 90percent). ‘HNMR(400 MHz, CDC13): 7.36 (s, 1H), 7.23 (t, J= 7.6 Hz, 1H), 7.12 (d, J= 8.0 Hz, 1H), 6.97 (d, J= 8.0 Hz, 1H), 6.91 (td, J= 7.6, 1.0 Hz, 1H), 3.78 (s,3H), 3.71 (s, 2H). |
87% | at 20℃; for 18 h; | [00121] A solution of 2-(2-hydroxyphenyl)acetic acid (3.00 g, 19.7 mmol) in methanol (40 mL) was treated with sulfuric acid (0.95 mL, 17.8 mmol) and the reaction was stirred at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate (250 mL), and the solution was washed with water (2 x 150 mL) and with saturated aqueous sodium chloride (150 mL); dried over sodium sulfate; filtered and evaporated in vacuo to give the crude product. Recrystallization from hot hexanes gave methyl 2-(2-hydroxyphenyl)acetate (2.83 g, 87percent). 1H NMR (400 MHz, CDCI3): 5 7.20 (ddd, J = 7.7, 7.4, 1.8 Hz, I H), 7.09-7.11 (m, 1 H), 6.94 (dd, J = 8.0, 1.2 Hz, 1 H), 6.88 (ddd, J = 7.4, 7.4, 1.2 Hz, 1 H), 3.75 (s, 3H), 3.69 (s, 2H). |
87% | at 20℃; for 18 h; | A solution of 2-(2-hydroxyphenyl)acetic acid (3.00 g, 19.7 mmol) in methanol (40 mL) was treated with sulfuric acid (0.95 mL, 17.8 mmol) and the reaction was stirred at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate (250 mL), and the solution was washed with water (2 x 150 mL) and with saturated aqueous sodium chloride (150 mL); dried over sodium sulfate; filtered and evaporated in vacuo to give the crude product. Recrystallization from hot hexanes gave methyl 2-(2-hydroxyphenyl)acetate (2.83 g, 87percent). 1H NMR (400 MHz, CDCI3): δ 7.20 (ddd, J = 7.7, 7.4, 1.8 Hz, 1 H), 7.09-7.11 (m, 1 H), 6.94 (dd, J = 8.0, 1.2 Hz, 1 H), 6.88 (ddd, J = 7.4, 7.4, 1.2 Hz, 1 H), 3.75 (s, 3H), 3.69 (s, 2H). |
2.8 g | for 10 h; Reflux | Preparation Example 4 Synthesis of (methyl 2-methoxymethoxy phenyl) acetate (0096) 3.04 g (20.0 mmol) of 2-hydroxyphenyl acetic acid was dissolved in 20 ml of methanol, and 1.0 ml of concentrated sulfuric acid was added thereto. The reaction solution was refluxed for 10 hours, and then distilled under reduced pressure for concentration. The concentrate was subjected to column chromatography to obtain 2.78 g (16.7 mmol) of (methyl 2-hydroxyphenyl) acetate. 2.8 g (20.0 mmol) of K2CO3 was again added to a solution obtained by dissolving the aforementioned compound in 20 ml of acetone, 2.40 g (30.0 mmol) of chloromethyl methyl ether was slowly added thereto for 30 minutes while the resulting solution was vigorously stirred at room temperature, and the mixture was vigorously stirred overnight. Then, the reaction solution was filtered to remove solid ingredients, the filtrate was distilled under reduced pressure for concentration, and then the concentrate was purified by silica gel column chromatography to obtain 2.56 g (12.3 mmol) of (2-methoxymethoxy phenyl) acetic methyl ester. (0097) 1H-NMR (CDCl3): 7.239 (t, 1H, J=8.0 Hz), 7.201 (d, 1H, J=8.0 Hz), 7.099 (d, 1H, J=8.0 Hz), 6.973 (t, 1H, J=8.0 Hz), 5.191 (s, 2H), 3.687 (s, 3H), 3.666 (s, 2H), 3.459 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With hydrogenchloride In methanol | Step 1 (2-hydroxy-phenyl)-acetic acid methyl ester To a solution of 2-hydroxyphenylacetic acid (20.0 g, 129.7 mmol) in 250 mL of methanol was bubbled at room temperature anhydrous hydrochloric acid for 5 minutes. The reaction was capped and stirred overnight. The reaction was then concentrated under reduced pressure to yield a pale oil (20.5 g, 95percent). 1 H NMR (300 MHz, DMSO): δ 9.45 (s, 1H), 7.15 (m, 2H), 6.75 (m, 2H), 3.57 (d, 2H), 3.35 (s, 3H). |
80% | With sulfuric acid In methanol; silica gel; toluene | (a) Methyl (2-Hydroxyphenyl)acetate A solution of 15 gm (0.1 mole) of 2-hydroxyphenylacetic acid in 500 ml methanol and 2 ml concentrated sulfuric acid was placed in a Soxhlet extractor charged with 3 A molecular sieves. The solution was heated to reflux for 72 hours, and the sieves were exchanged at 24-hour intervals. The reaction medium was then evaporated to an oil which was dissolved in 100 ml toluene and extracted with 3*100 ml portions of water. The toluene phase was dried over magnesium sulfate, treated with activated charcoal and evaporated to provide 13 gm (80percent yield) of a yellow oil. The NMR spectrum was consistent with the assigned structure and this material was used in the next reaction step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With hydrogenchloride; sodium hydrogencarbonate In methanol | EXAMPLE 3 This Example illustrates the preparation of (E)-methyl 2-[2'-(5"-nitropyridin-2"-yloxy)phenyl]-3-methoxyacrylate (Compound No. 133 of Table I). 2-(Hydroxyphenyl)acetic acid (50 g) was added to a solution of hydrogen chloride in methanol [prepared from acetyl chloride (25 ml) and methanol (250 ml)]. The solution was stirred at room temperature for three hours and then allowed to stand overnight (fifteen hours). The resulting mixture was concentrated under reduced pressure, and the residue was taken up in ether (250 ml) and washed with an aqueous solution of sodium bicarbonate until effervescence ceased. The ethereal solution was dried and then concentrated under reduced pressure and the resulting solid was recrystallized from ether/petrol to afford methyl (2-hydroxyphenyl)acetate (50 g; 92percent yield) as white, powdery crystals, mp. 70°-72° C.; infrared max. (nujol mull): 3420, 1715 cm-1; 1 H nmr (90 MHz); delta 3.70 (2H,s), 3.75 (3H,s), 6.80-6.95 (2H,m), 7.05-7.10 (1H,m), 7.15-7.25 (1H,m), 7.40 (1H,s)ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With hydrogenchloride; sodium hydrogencarbonate In methanol | EXAMPLE 1 This Example illustrates the preparation of E-methyl 3-methoxy-2-[2'-(benzoxazol-2"-yloxyphenyl)]propenoate (Compound No. 44 of Table I). 2-Hydroxyphenylacetic acid (50 g) was added to a solution of hydrogen chloride in methanol [prepared from acetyl chloride (25 ml) and methanol (250 ml)]. The solution was stirred at room temperature for three hours and then allowed to stand overnight (fifteen hours). The resulting mixture was concentrated under reduced pressure, and the residue was taken up in ether (250 ml) and washed with an aqueous solution of sodium bicarbonate until effervescence ceased. The ethereal solution was dried and then concentrated under reduced pressure and the resulting solid was recrystallized from ether/petrol to afford methyl 2-hydroxyphenylacetate (50 g; 92percent yield) as white, powdery crystals, M.P. 70°-72° C.; infrared maxima (nujol mull): 3420, 1715 cm-1; 1 H nmr (CDCl3, 90 MHz): delta 3.70 (2H, s), 3.75 (3H,s), 6.80-6.95 (2H,m), 7.05-7.10 (1H,m), 7.15-7.25 (1H,m), 7.40 (1H,s)ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With hydrogenchloride; sodium hydrogencarbonate In methanol | EXAMPLE 1 This Example illustrates the preparation of E-methyl 2-[2'-(6"-chloropyrazin-2"-yloxy)phenyl]-3-methoxypropenoate (Compound No. 2 of Table I). 2-Hydroxyphenylacetic acid (50 g) was added to a solution of hydrogen chloride in methanol [prepared from acetyl chloride (25 ml) and methanol (250 ml)]. The solution was stirred at room temperature for three hours and then allowed to stand overnight (fifteen hours). The resulting mixture was concentrated under reduced pressure, and the residue was taken up in ether (250 ml) and washed with an aqueous solution of sodium bicarbonate until effervescence ceased. The ethereal solution was dried and then concentrated under reduced pressure and the resulting solid was recrystallized from ether/petrol to afford methyl 2-hydroxyphenylacetate (50 g; 92percent YIELD) as white, powdery crystals, M.P. 70°-72° C.; infrared maxima (nujol mull): 3420, 1715 cm-1; 1 H nmr (CDCl3, 90 MHz): delta 3.70 (2H, s), 3.75 (3H, s), 6.80-6.95 (2H, m), 7.05-7.10 (1H, m), 7.15-7.25 (1H, m), 7.40 (1H, s) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | at 20℃; for 18 h; | 2-(2-hydroxyphenyl)acetic acid (484 g, 3.18 mol) was dissolved in methanol, and then tetrabutylammonium tribromide (1549 g, 3.18 mol) was added to the solution. The resulting mixture was allowed to stir at room temperature for 18 hours. After evaporation of solvent in vacuo, the residue obtained was dissolved in EtOAc. The organic layer was washed with 1 N HC1, water and brine, dried and concentrated, the residue obtained was purified using flash column chromatography on silica gel (eluted with PE / EtOAc = 10 / 1) to give pure methyl 2-(5-bromo-2-hydroxyphenyl)acetate (750 g, 94percent). 1H- MR (400 MHz, CDC13) δ 7.48 (br s, 1H), 7.20-7.25 (m, 2H), 6.75-6.78 (m, 1H), 3.74 (s, 3H), 3.62 (s, 2H). MS (M+H)+: 245. |
90% | at 20℃; for 18 h; | 2-(2-hydroxyphenyl)acetic acid (100 g, 0.66 mol) was dissolved in MeOH, and then TBATB (320 g, 0.66 mmol) was added to the solution. The resulting mixture was stirred at RT for 18 hours. After evaporation of solvent, the residue was dissolved in diethyl ether. The organic layer was washed with 1 N HC1, 2 M sodium bisulfate, H20 and brine, dried and evaporated to yield methyl 2-(5-bromo-2-hydroxyphenyl)acetate (145 g, yield: 90percent) 1H-NMR (400 MHz, CDCl3) δ 7.48 (br s, 1H), 7.20-7.25 (m, 2H), 6.75-6.78 (m, 1H), 3.74 (s, 3H), 3.62 (s, 2H). MS (M+H)+: 245. |
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