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CAS No. : | 60563-13-5 | MDL No. : | MFCD00009180 |
Formula : | C11H14O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | AWPMWZHWVKXADV-UHFFFAOYSA-N |
M.W : | 210.23 | Pubchem ID : | 108965 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.36 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 55.63 |
TPSA : | 55.76 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) : | -6.86 cm/s |
Log Po/w (iLOGP) : | 2.15 |
Log Po/w (XLOGP3) : | 1.02 |
Log Po/w (WLOGP) : | 1.51 |
Log Po/w (MLOGP) : | 1.38 |
Log Po/w (SILICOS-IT) : | 1.97 |
Consensus Log Po/w : | 1.6 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.75 |
Solubility : | 3.72 mg/ml ; 0.0177 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.78 |
Solubility : | 3.48 mg/ml ; 0.0166 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.84 |
Solubility : | 0.302 mg/ml ; 0.00144 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.88 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P301+P312-P302+P352-P304+P340-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% | With tetra-(n-butyl)ammonium iodide; caesium carbonate; In acetone; for 21.5h;Heating / reflux; | EXAMPLE 10 Preparation of 4-(2,4-dichloro-5-methoxy-phenylamino)-5-[3-methoxy-4-(2-methoxy-ethoxy)-phenyl]-nicotinonitrile 149 To a stirred solution of <strong>[60563-13-5]ethyl homovanillate</strong> (16.2 g, 77.05 mmol), tetrabutylammonium iodide (TBAI, 1.42 g, 3.85 mmol), and 2-bromoethylmethyl ether (10.4 mL, 115.5 mmol) in 250 mL of acetone was added cesium carbonate (Cs2CO3, 40.16 g, 123.2 mmol). The mixture was stirred for 21.5 hours at reflux. The mixture was concentrated and the residue was extracted from water with EtOAc. The combined organic extracts were then dried over Na2SO4, filtered, and concentrated in vacuo to yield 27 g of orange oil. The oil was purified by flash chromatography using silica gel and 10-60% EtOAc/hexane. Combined fractions were concentrated to give 20.67 g (100%) of [3-methoxy-4-(2-methoxyethoxy)phenyl]acetic acid ethyl ester as a colorless oil. To a 500 mL three-necked round-bottomed flask was added 100 mL of anhydrous THF and cooled to -78oC. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | Example 79 To a mixture of 3- {3-propyl-l- [5- (trifluoromethyl)-2-pyridyl]-lH-pyrazol-4-yl}-1-propanol (470 mg), ethyl 4- hydroxy-3-methoxyphenylacetate (320 mg), tributylphosphine (610 mg) and tetrahydrofuran (30 ml) was added 1,1'- azodicarbonyldipiperidine (760 mg) at room temperature and the mixture was stirred overnight. The reaction solution was concentrated. The residue was subjected to silica gel column chromatography, and a colorless oil was obtained from a fraction eluted with ethyl acetate-hexane (1: 4, volume ratio). A mixture of the obtained oily substance, 1N aqueous sodium hydroxide solution (5 ml), tetrahydrofuran (5 ml) and methanol (5 ml) was stirred at room temperature for 5 hours. 1N Hydrochloric acid (5 ml) was added and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried(MgS04) and concentrated. The obtained colorless crystals were collected by filtration to give [3-methoxy-4- (3- {3-propyl-l-[5-(trifluoromethyl)-2-pyridyl]-lH-pyrazol-4-yl} propoxy) phenyl] acetic acid (550 mg, yield77%). The crystals were recrystallized from ethyl acetate-hexane. melting point:121-122 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | Example 278 To a mixture of3- {1- [5- (trifluoromethyl)-2-pyridyl]-3-isopropyl-lH-pyrazol-4-yl}-1-propanol (400 mg), ethyl (4- hydroxy-3-methoxyphenyl) acetate (280 mg), tributylphosphine (520 mg) and tetrahydrofuran (50 ml) was added 1,1'- azodicarbonyldipiperidine (650 mg) at room temperature and the <Desc/Clms Page number 467>mixture was stirred overnight. The reaction solution was concentrated. The residue was subjected to silica gel column chromatography, and a colorless oil was obtained from a fraction eluted with ethyl acetate-hexane (1: 4, volume ratio). A mixture of the obtained oily substance, 1N aqueous sodium hydroxide solution (1.5 ml), tetrahydrofuran (4 ml) and methanol (4 ml) was stirred at room temperature for 5 hours. 1N Hydrochloric acid (1.5 ml) was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried(MgS04) and concentrated. The obtained colorless crystals were collected by filtration to give[3-methoxy-4- (3- {1- [5-(trifluoromethyl)-2-pyridyl]-3-isopropyl-lH-pyrazol-4-yl} propoxy) phenyl] acetic acid (250 mg, yield41%). The crystals were recrystallized from ethyl acetate-hexane. melting point:134-135 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With pyridine; In dichloromethane; at 0℃; for 3h; | To a cooled solution of ethyl 4-hydroxy-3-methoxyphenylacetate (4a; 13.7 g; 65.2 mmol) and 260 mL of CH2Cl2 under N2 atmosphere was added dropwise triflic anhydride (16 mL; 97.9 mmol) followed by dropwise addition of pyridine (8.9 mL; 8.8 mmol). The reaction was stirred in an ice-water bath for 3 h. The solution was transferred to a separatory funnel and washed with water and brine, dried (Na2SO4), filtered and evaporated. to yield 21 g (90%) of 4b. |
90% | With pyridine; In dichloromethane; at 0℃; | To a cooled solution of ethyl 4-hydroxy-3-methoxyphenylacetate (4a; 13.7 g; 65.2 mmol) and 260 mL of CH2Cl2 under N2 atmosphere was added dropwise triflic anhydride (16 mL; 97.9 mmol) followed by dropwise addition of pyridine (8.9 mL; 8.8 mmol). The reaction was stirred in an ice-water bath for 3 h. The solution was transferred to a separatory funnel and washed with water and brine, dried (Na2SO4), filtered and evaporated to yield 21 g (90%) of 4b. |
Ethyl (4-hydroxy-3-methoxyphenyl) acetate, 12 g, 57 mmol] was dissolved in anhydrous dichloromethane (200 mL). 4-Dimethylammopyridme (0.70 g, 0.10 equiv) was added, followed by triethylamine (9.6 mL, 69 mmol). The solution was then cooled to -78 0C in a dry ice and acetone bath while under nitrogen. Trifluoromethanesulfonic anhydride (9.6 mL, 57 mmol) was slowly added and the reaction mixture was allowed to warm to ambient temperature. The reaction mixture was then diluted with dichloromethane (200 mL) and washed with water (2 x 100 mL). The organic layer was dried over MgSO4, filtered, and concentrated to dryness under reduced pressure to yield ethyl (3-methoxy-4-[(trifluoromethyl)sulfonyl]oxy}phenyl)acetate, which was used without further purification. LC/MS [(M+l)- CO2Et]+ = 269.0; tR = 3.5 min |
With dmap; triethylamine; In dichloromethane; at 20℃;Inert atmosphere; Cooling with acetone-dry ice; | Step A: Ethyl (3-Methoxy-4-{r(trifluoromethyl)sulfonyl1oxylphenyl)acetate Ethyl (4-hydroxy-3-methoxyphenyl) acetate (12.0 g, 57 mmol) was dissolved in anhydrous dichloromethane (200 mL). 4-Dimethylaminopyridine (0.70 g, 0.10 equiv) was added, followed by triethylamine (9.6 mL, 69 mmol). The solution was then cooled to in a dry ice and acetone bath while under nitrogen. Trifluoromethanesulfonic anhydride (9.6 mL, 57 mmol) was slowly added and the reaction mixture was allowed to warm to ambient temperature. The reaction mixture was then diluted with dichloromethane (200 mL) and washed with water (2 x 100 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated to dryness under reduced pressure to provide ethyl (3-methoxy-4-[(trifluoromethyl)sulfonyl]oxy}phenyl)acetate which was used directly in the next step without further purification. LC/MS [(M+l)- C02Et]+ = 269.0;. | |
With dmap; triethylamine; In dichloromethane; at 20℃;Inert atmosphere; | Step A: Ethyl (3-methoxy-4- { [(trifluoromethyl) sulfonyl] oxy} phenyl)acetate: Ethyl (4-hydroxy-3-methoxyphenyl) acetate, 12.0 g, 57 mmol was dissolved in anhydrous dichioromethane (200mL). 4-Dimethylaminopyridine (0.70 g, 0.10 equiv) was added, followed by triethylamine (9.6mL, 69 mmol). The solution was then cooled to in a dry ice and acetone bath while undernitrogen. Trifluoromethanesulfonic anhydride (9.6 mL, 57 mmol) was slowly added and the reaction mixture was allowed to warm to ambient temperature. The reaction mixture was then diluted with dichloromethane (200 mL) and washed with water (2 x 100 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated to dryness under reduced pressureto yield the triflate. LC/MS [(M+1)- CO2Et] = 269.0;. | |
With dmap; triethylamine; In dichloromethane; at 20℃;Cooling with acetone-dry ice; Inert atmosphere; | The crude phenol [ethyl (4-hydroxy-3-methoxyphenyl) acetate, 12.0 g, 57 mmol] was dissolved in anhydrous dichloromethane (200 mL). 4-Dimethylaminopyridine (0.70 g, 0.10 equiv) was added, followed by triethylamine (9.6 mL, 68 mmol). The solution was then cooled to in a dry ice and acetone bath while under nitrogen. Trifluoromethanesulfonic anhydride (9.6 mL, 57 mmol) was slowly added and the reaction mixture was allowed to warm to ambient temperature. The reaction mixture was then diluted with dichloromethane (200 mL) and washed with water (2 x 100 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated to dryness under reduced pressure to yield the crude triflate. LC-MS (IE, m/z): 269.0 [(M+1)-CO2Et]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate; In acetonitrile; at 20℃; for 72h; | A solution of 2- [1- (2-bromoethyl) pentyl]-3-methyl-6- (trifluoromethyl)-1-benzothiophene (60 mg, 0.15 mmol) in anhydrous MeCN (2.5 mL) was treated with cesium carbonate (150 mg) and a solution of ethyl [4-hydroxy-3- (methyloxy) phenyl] acetate (112 mg, 0.5 mmol) in anhydrous MeCN (2.5 mL). The mixture was stirred at 20C under nitrogen for 3 days, and then evaporated to dryness and eluted through a 5 g SPE silica cartridge with EtOAc: cyclohexane (1: 20) to afford the title compound as a gum (32 mg).'H NMR (400 MHz; CDCI3) 8 : 0.84 (3H, t, J 7 Hz), 1.16-1. 34 (4H, m), 1.24 (3H, t, J 7 Hz), 1.68 (1 H, m), 1.82 (1 H, m), 2.02 (1 H, m), 2.29 (3H, s), 2.35 (1 H, m), 3.52 (2H, s), 3.52 (1 H, m), 3.74 (1 H, m), 3.84 (3H, s), 3.95 (1 H, m), 4.14 (2H, q, J 7 Hz, 6.65 (1 H, d, J 8 Hz), 6.71 (1 H, dd, J 8 Hz, 2 Hz), 6.80 (1 H, d, J 2 Hz), 7.56 (1H, d, J 8 Hz), 7.66 (1H, d, J 8 Hz), 8.04 (1H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With pyridine; trifluoromethylsulfonic anhydride; In dichloromethane; at 0℃; for 3h; | To a cooled solution of ethyl 4-hydroxy-3-methoxyphenylacetate (4a; 13.7 g; 65.2 mmol) and 260 mL of CH2Cl2 under N2 atmosphere was added dropwise triflic anhydride (16 mL; 97.9 mmol) followed by dropwise addition of pyridine (8.9 mL; 8.8 mmol). The reaction was stirred in an ice-water bath for 3 h. The solution was transferred to a separatory funnel and washed with water and brine, dried (Na2SO4), filtered and evaporated to yield 21 g (90%) of 4b |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In dichloromethane; acetone; | EXAMPLE 66 3-Methoxy-4-(tetradecyloxy)benzeneacetic acid ethyl ester A mixture of 50 g of <strong>[60563-13-5]3-methoxy-4-hydroxybenzeneacetic acid ethyl ester</strong>, 66.1 g of powdered potassium carbonate, 70.57 g of 1-bromotetradecane and 500 ml of acetone is heated at reflux temperature for 76 hours. The reaction is cooled, filtered and the filtrate concentrated in vacuo. The residue is dissolved in methylene chloride, washed with 2% sodium bicarbonate and saturated sodium chloride, dried and concentrated in vacuo. The residue is purified by column chromatography (silica gel:0-10% ethyl acetate/hexane) to give 66.6 g of the desired product as colorless crystals. MP 40-41 C. EI-MS:m/z 406 (M+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; methyltertbutyl ether; | A) 5 g of 4-hydroxy-3-methoxyphenyl ethyl acetate were dissolved in 25 ml dichloromethane. 15.3 g of N-(ethyl)-diisopropylamine and 12.65 ml of 2-(trimethylsilyl)-ethoxymethyl chloride were added to the solution. The reaction mixture was stirred for 1.5 hours at room temperature. For workup, the reaction mixture was then shaken with water. The dichloromethane phase was separated and concentrated to dryness. The oil obtained was dissolved in methyl-tert-butyl ether and shaken with water once more. The organic phase was dried with sodium sulfate, filtered, and concentrated. 7.8 g of 4-[2-(trimethylsilyl)-ethoxymethoxy]-3-methoxyphenyl ethyl acetate were obtained as an oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With potassium carbonate; In water; acetone; | Step 1) Synthesis of ethyl 4-(2-chloroethoxy)-3-methoxy-phenylacetamide 46.4 g (0.216 mol) of <strong>[60563-13-5]ethyl homovanillate</strong>(ehtyl 4-hydroxy-3-methoxyphenylacetate) and 91.7 ml (1.08 mol) of 1-bromo-2-chloroethane were dissolved in 294 ml of acetone and 90.0 g (0.648 mol) of potassium carbonate was added thereto. The mixture was refluxed for 42 hours and 200 ml of water was added thereto, which was extracted with 500 ml of dichloromethane. The organic layer was washed successively with 100 ml of 0.1N aqueous NaCl solution and 100 ml of water; then the solvent was distilled off under a reduced pressure to obtain 51.7 g of the title compound as a yellow solid(yield: 88%). m.p.: 51-55 C. 1 H NMR(200 MHz, CDCl3) delta1.26(t, 3H, J=7.2 Hz, CH2), 3.56(s, 2H, ArCH2), 3.85(t, 2H, J=6.2 Hz, CH2 Cl), 3.87(s, 3H, OCH3), 4.16(q, 2H, J=7.2 Hz, CO2 CH2), 4.26(t, 2H, J=6.2 Hz, ArOCH2), 6.70-6.84(m, 3H, ArH) |
88% | With potassium carbonate; In water; acetone; | Step 1) Synthesis of ethyl 4-(2-chloroethoxy)-3-methoxyphenylacetamide 46.4g(0.216 mol) of <strong>[60563-13-5]ethyl homovanillate</strong>(ehtyl 4-hydroxy-3-methoxyphenylacetate) and 91.7ml(1.08 mol) of 1-bromo-2-chloroethane were dissolved in 294ml of acetone and 90.0g(0.648 mol) of potassium carbonate was added thereto. The mixture was refluxed for 42 hours and 200ml of water was added thereto, which was extracted with 500ml of dichloromethane. The organic layer was washed successively with 100ml of 0.1N aqueous NaCl solution and 100ml of water; then the solvent was distilled off under a reduced pressure to obtain 51.7g of the title compound as a yellow solid(yield: 88%). m.p.: 51-55C 1H NMR(200MHz, CDCl3) delta 1.26(t, 3H, J=7.2Hz, CH2), 3.56(s, 2H, ArCH2), 3.85(t, 2H, J=6.2Hz, CH2Cl), 3.87(s, 3H, OCH3), 4.16(q, 2H, J=7.2Hz, CO2CH2), 4.26(t, 2H, J=6.2Hz, ArOCH2), 6.70-6.84(m, 3H, ArH) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44.4 g (65%) | With potassium carbonate; In acetone; | PREPARATION 41 4-(3-Chloropropoxy)-3-methoxybenzeneacetic acid ethyl ester A mixture of 50 g (0.238 mole) of <strong>[60563-13-5]ethyl homovanillate</strong>, 75 g (0.476 mole) of 1-bromo-3-chloropropane and 98.7 g (0.71 mole) of anhydrous potassium carbonate in 1 liter of acetone was heated at reflux for 24 hr. The mixture was filtered and the filtrate was concentrated under reduced pressure to give an oil which gradually crystallized to a semi-solid. The solid was recrystallized from ethyl ether-petroleum ether (30-60 C.) to yield 44.4 g (65%) of white solid, m.p. 36-38 C. Analysis: Calculated for C14 H19 ClO4: C, 58.64; H, 6.68. Found: C, 58.74; H, 6.74. |
44.4 g (65%) | With potassium carbonate; In acetone; | PREPARATION 12 4-(3-Chloropropoxy)-3-methoxybenzeneacetic acid ethyl ester. A mixture of 50 g (0.238 mole of <strong>[60563-13-5]ethyl homovanillate</strong> (98% Aldrich), 75 g (0.476 mole) of 1-bromo-3-chloropropane and 98.7 g (0.71 mole) of anhydrous potassium carbonate in 1 L of acetone was heated at reflux for 24 hr. The mixture was filtered and the filtrate was concentrated under reduced pressure to give an oil which gradually crystallized to a semi-solid. The solid was recrystallized from ethyl ether-petroleum ether (30-60) to yield 44.4 g (65%) of title compound a white solid, mp 36-38 C. |
44.4 g (65%) | With potassium carbonate; | PREPARATION 6 4-(3-Chloropropoxy)-3-methoxybenzeneacetic acid ethyl ester A mixture of 50 g (0.238 mole) of <strong>[60563-13-5]ethyl homovanillate</strong> (98%), 75 g (0.476 mole) of 1-bromo-3-chloropropane and 98.7 g (0.71 mole) of anhydrous potassium carbonate in 1 liter of actone was heated at reflux for 24 hr. The mixture was filtered and the filtrate was concentrated under reduced pressure to give an oil which gradually crystallized to a semi-solid. The solid was recrystallized from ethyl ether-petroleum ether (30-60 C.) to yield 44.4 g (65%) of the title compound as a white solid, mp 36-38 C. Analysis: Calculated for C14 H19 ClO4: C, 58.64; H, 6.68. Found: C, 58.74; H, 6.74. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium iodide; sodium chloride; potassium carbonate; In N-methyl-acetamide; water; | EXAMPLE 2 100 ml of dimethylformamide were added to 10.0 g of ethyl 3-methoxy-4-hydroxyphenylacetate, 11.8 g of potassium iodide and 13.1 g of potassium carbonate, and then 8.1 ml of 3-chloro-3 methyl-1-butyne were added dropwise and the mixture was stirred at 70 to 80 C. for 20 hours. After cooling, water was added to the mixture, which was extracted with ether; the ether layer was washed with water, 10% sodium hydroxide and a saturated solution of sodium chloride, and dried over anhydrous sodium sulfate; the solvent was distilled off; and the residue was purified by column chromatography on silica gel (benzene/ethyl acetate=10/1) to give 6.0 g of ethyl 3-methoxy-4-(1,1-dimethylpropargyloxy)phenylacetate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 100℃; for 5h; | To a solution of (4-hydroxy-3-methoxy-phenyl)-acetic acid ethyl ester (34, 2.0 g, 9.51 mmol) in NMP (10 mL) was added K2CO3 (3.94 g, 28.5 mmol) and 16 (1.48 g, 9.51 mmol). The reaction was heated at 100 C. for 5 h. The reaction mixture was cooled to RT and HCl (10%) was added. The mixture was extracted 3 times with EtOAc. The combined organics were washed with H2O and brine, dried over Na2SO4, filtered and evaporated in vacuo. The crude product was purified by SiO2 chromatography eluding with hexane/EtOAc to afford 35. Steps 2-4 were run as described for steps 2-4 of example 1, except in step 4, 4-amino-3-methyl-benzenesulfonamide was used in place of 4-amino-benzenesulfonamide which afforded I-51. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With caesium carbonate; In dimethyl sulfoxide; at 20 - 100℃; for 2h; | To a solution of l-fluoro-4-iodo-2-nitrobenzene (9.13 g, 34.20 mmol) and ethyl 2-(4-hydroxy- 3-methoxyphenyl)acetate (7.19 g, 34.20 mmol) in DMSO (100 mL), CsCO3 (12.26 g, 37.62 mmol) was added at room temperature. The mixture was heated at 10O0C for 2h. The reaction was diluted with ethyl acetate and washed with water, saturated brine, dried over <n="79"/>Na2SO4, filtered, and concentrated under reduced pressure to give a white solid. The residue was used without further purification. MS ESI (pos.) m/z: 458.0 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In butanone; at 20℃; for 24h;Heating / reflux; | Delivery agent 3: 4-(cvclobutylmethoxy)-3-methoxyphenyllacetic acid[65] To a stirred solution of ethyl ethyl (4-hydroxy-3-methoxyphenyl)acetate (1.05 g, 5.0mmol ) and potassium carbonate ( 1.38 g, lOmmol) in 40 mL of 2-butanone at ambient temperature was added in one portion of (bromomethyl)cyclobutane ( 97% pure) ( 1.53g, lO.Ommol). The stirred reaction mixture was heated at reflux for 24 hr. HPLC revealed the disappearance of the starting material of ethyl (4-hydroxy-3-methoxyphenyl)acetate. The mixture was allowed to cool to ambient temperature. The solid was filtered off. The filter cake was washed with acetone. The combined filtrate was concentrated in vacuo to nearly dryness. Methanol was added (5 mL) was added to the residue, followed by the addition of a 2-N aqueous solution of NaOH ( 2OmL, 40mmol). The reaction was stirred overnight at about 40 C. HPLC indicated that the saponification was completed, and revealed one single peak signal of the expected carboxylic acid. The reaction mixture was subjected to roto- vaporation to remove methanol. Ice was added to the basic aqueous solution. The acidification with a 25 mL of HCl aqueous 2N solution (50 mmol) led to the immediate precipitation of a white solid. Stirring was continued for an additional 30 min. and then the precipitation was filtered off with suction through a sintered glass funnel. The collected solid was successively washed with three 50-mL portions of water, and two 25-mL portions of hexane. The collected solid was dried in vacuo for two days at ambient temperature to afford 1.20 g ( 95 %) of [4-(cyclobutylmethoxy)-3-methoxyphenyl] acetic acid as a white solid.[66] HPLC: R1: 4.87 min. 1H NMR (400 MHz DMSO- d6 ): delta 1.78-1.87 (m, 4H ), 2.05 (m, 2H), 2.67 (m, IH ), 3.46 (s, 2H), 3.76 (s, 3H), 3.88 (m, 2H ), 6.74 ( m, IH ), 6.83- 6.86 (m, 2H ), 12.21 ( s, IH ). 13C NMR (100 MHz DMSO-d6 ): delta 23.49, 29.84, 39.50, 45.60, 60.93, 77.89, 118.76, 118.99, 126.81, 132.92, 152.48, 154.20, 178.26. LC/MS m/z: 251 [(M+ 1)+]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | 0.9 g (23 mmol) of 60% sodium hydride is added in portions to a previously cooled solution of 4 g (19 mmol) of (4-hydroxy-3-methoxy-phenyl)-ethyl acetate in 20 ml of tetrahydrofuran and 20 ml of dimethylformamide. After stirring at room temperature for 45 minutes, 2.4 ml (21 mmol) of 1-chloromethoxy-2-methoxy-ethane is added dropwise. After stirring at room temperature for 1 hour, water and ethyl acetate are added. The organic phase is washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered, and evaporated. 5.5 g (97%) of [3-methoxy-4-(2-methoxy-ethoxymethoxy)-phenyl]-ethyl acetate is obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With sulfuric acid; for 2h;Reflux; | The compound 2-(3-ethoxy-4-hydroxyphenyl)acetic acid (a3) (5.5 g, 28 mmol) was dissolved in 50 ml of ethanol, concentrated sulfuric acid (1 ml) was added, and the mixture was reacted under reflux for 2 h. The reaction was completed by a thin-layer chromatography plate, and the solvent was evaporated to dryness under reduced pressure. The solvent was dissolved in ethyl acetate, washed with saturated brine (1×), washed with saturated sodium hydrogen carbonate (1×), and brine (1×), The residue was dried with MgSO 4, filtered and evaporated |
With sulfuric acid; at 90℃; for 7h; | Excess of the corresponding alcohol. <strong>[306-08-1]Homovanillic acid</strong> (1.5-3 g) was stirred in the respectivealcohol (100 mL) with 0.2-0.5 equivalents of sulfuric acid for 7 h at 90 C (heating block temperature).Most of the alcohol was removed in vacuo, then sat. aq. NaHCO3 solution and EtOAc were added.The organic phase was separated and the aqueous phase extracted with EtOAc. The combined organiclayer was washed with sat. aq. NaHCO3 solution and water or alternatively with sat. aq. NaCl solution,dried over NaSO4 and the solvent removed in vacuo. The product was obtained after purification bycolumn chromatography on silica in 90% to quantitative yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; for 15h;Inert atmosphere; | To a solution of 10 (5.00 g, 23.8 mmol), 11 (6.22 g, 30.9 mmol) and PPh3 (9.36 g, 35.7 mmol) in THF (79 mL) was added diisopropyl azodicarboxylate (7.52 mL, 35.7 mmol) at room temperature. The reaction mixture was stirred at room temperature for 15 h and then concentrated. The residue was purified by silica gel chromatography (EtOAc/n-hexane = 1/3) to afford a pale yellow oil. To a CHCl3 (5 mL) solution of the oil was added 4 M HCl in 1,4-dioxane (50 mL) at room temperature. The reaction mixture was stirred at room temperature for 1 h and then concentrated. Trituration with Et2O (40 mL) and filtration of the solid gave 12 (5.66 g, 72%) as a white solid; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With di-tert-butyl-diazodicarboxylate; In dichloromethane; at 20℃; for 3h; | Intermediate 1.1: [4-((R)-sec-Butoxy)-3-methoxy-phenyl]-acetic acid ethyl ester To a solution of <strong>[60563-13-5](4-hydroxy-3-methoxy-phenyl)-acetic acid ethyl ester</strong> (700 mg, 3.33 mmol) in DCM (40 ml) were successively added (S)-butan-2-ol (0.37 ml, 4.0 mmol), supported PPh3 (loading of 1.52 mmol/g, 4.38 g, 6.66 mmol) and DTAD (1.15 g, 5.0 mmol). The reaction mixture was shaken at RT for 3 h, then filtered and the resin was washed with DCM. The filtrate was evaporated to dryness and the resulting residue was purified by Combi-Flash Companion (Isco Inc.) column chromatography (SiO2; gradient elution, heptane/TBME 95:5?1:1) to yield the title compound (818 mg, 3.07 mmol, 92%) as a colorless oil. TLC: RF=0.85 (heptane/DCM/TBME 1:1:2); HPLC: BtRet=2.46 min; API-MS: m/z 267.2 [M+H]+; 1H NMR (400 MHz, CDCl3): 1.00 (t, J=7.5, 3H), 1.28 (t, J=7.1, 3H), 1.33 (d, J=6.1, 3H), 1.60-1.70 (m, 1H), 1.77-1.89 (m, 1H), 3.56 (s, 2H), 3.86 (s, 3H), 4.17 (q, J=7.1, 2H), 4.25 (sxt, J=6.1, 1H), 6.79 (dd, J=8.3, 2.0, 1H), 6.83-6.87 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Intermediate 26.1: (4-Hydroxy-3-methoxy-phenyl)-acetic acid A mixture of (4-hydroxy-3-methoxy-phenyl)-acetic acid ethyl ester (2 g, 9.51 mmol) and LiOH monohydrate (1.2 g, 28.5 mmol) in MeOH (20 ml) and water (10 ml) was stirred at RT for 14 h. The reaction mixture was concentrated under vacuum, diluted into water and neutralized by the addition of HCl 2 M in water (14.3 ml). The resulting slurry was extracted with DCM (3*) and AcOEt (2*) and the combined organic fractions were dried over Na2SO4, filtered and evaporated to dryness to yield the crude title compound (1.67 g, 9.17 mmol, 96%) as a brownish solid, which was used in the next step without further purification. HPLC: AtRet=0.77 min; LC-MS: m/z 183.4 [M+H]+; 1H NMR (400 MHz, DMSO-d6): 3.43 (s, 2H), 3.74 (s, 3H), 6.61-6.66 (m, J=8.1, 2.0, 1H), 6.67-6.72 (m, 1H), 6.81 (d, J=2.0, 1H), 8.81 (s, 1H), 12.17 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | A mixture of ethyl <strong>[60563-13-5](4-hydroxy-3-methoxy-phenyl)-acetic acid ethyl ester</strong> (11.22 g, 53.4 mmol) and K2CO3 (22.13 g, 160 mmol) in DMF (100 ml) was heated at 60 C. 2-Iodopropane (9.06 ml, 91 mmol) was added and the mixture was vigorously stirred at 60 C. for 5 h. The reaction mixture was cooled to RT, diluted with AcOEt and washed with water. The aqueous phase was separated and further extracted with AcOEt. The combined organic fractions were dried over Na2SO4, filtered and evaporated to dryness. The resulting crude material was purified by Combi-Flash Companion (Isco Inc.) column chromatography (SiO2; gradient elution, heptane/AcOEt 98:2?3:1) to yield the title compound (11.94 g, 47.3 mmol, 89%) as a colorless oil. TLC: RF=0.44 (heptane/AcOEt 7:3); HPLC: AtRet=2.14 min; LC-MS: m/z 253.4 [M+H]+; 1H NMR (400 MHz, CDCl3): 1.28 (t, J=7.1, 3H), 1.38 (d, J=6.1, 6H), 3.56 (s, 2H), 3.87 (s, 3H), 4.17 (q, J=7.1, 2H), 4.50 (h, J=6.1, 1H), 6.77-6.89 (m, 3H). | |
89% | With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 5h; | I opropoxy-3-methoxy-phenyl)-acetic acid ethyl esterA mixture of ethyl <strong>[60563-13-5](4-hydroxy-3-methoxy-phenyl)-acetic acid ethyl ester</strong> (1 1.22 g, 53.4 mmol) and K2C03 (22.13 g, 160 mmol) in DMF (100 ml) was heated at 60C. 2- lodopropane (9.06 ml, 91 mmol) was added and the mixture was vigorously stirred at 60C for 5h. The reaction mixture was cooled to RT, diluted with AcOEt and washed with water. The aqueous phase was separated and further extracted with AcOEt. The combined organic fractions were dried over Na2S04, filtered and evaporated to dryness. The resulting crude material was purified by Combi-Flash Companion (Isco Inc.) column chromatography (Si02; gradient elution, heptane / AcOEt 98:2? 3: 1 ) to yield the title compound (11.94 g, 47.3 mmol, 89%) as a colorless oil.TLC: RF = 0.44 (heptane / AcOEt 7:3);HPLC: A = 2.14 min; LC-MS: m/z 253.4 [M+H]+; 1H-NMR (400 MHz, CDCI3): delta 1.28 (t, J = 7.1 , 3H), 1.38 (d, J = 6.1 , 6H), 3.56 (s, 2H), 3.87 (s, 3H), 4.17 (q, J = 7.1 , 2H), 4.50 (h, J= 6.1, 1H), 6.77 - 6.89 (m, 3H). |
89% | With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 5h; | Intermediate 75.1: (4-Isopropoxy-3methoxy-phenyl)-acetic acid ethyl ester A mixture of ethyl<strong>[60563-13-5](4-hydroxy-3-methoxy-phenyl)-acetic acid ethyl ester</strong> (11.22 g, 53.4 mmol) and K2CO3 (22.13 g, 160 mmol) in DMF (100 ml) was heated at 60 C. 2-Iodopropane (9.06 ml, 91 mmol) was added and the mixture was vigorously stirred at 60 C. for 5 h. The reaction mixture was cooled to RT, diluted with AcOEt and washed with water. The aqueous phase was separated and further extracted with AcOEt. The combined organic fractions were dried over Na2SO4, filtered and evaporated to dryness. The resulting crude material was purified by Combi-Flash Companion (Isco Inc.) column chromatography (SiO2; gradient elution, heptane/AcOEt 98:2?3:1) to yield the title compound (11.94 g, 47.3 mmol, 89%) as a colorless oil. TLC: RF=0.44 (heptane/AcOEt 7:3); HPLC: AtRet=2.14 min; LC-MS: m/z 253.4 [M+H]+; 1H NMR (400 MHz, CDCl3): 1.28 (t, J=7.1, 3H), 1.38 (d, J=6.1, 6H), 3.56 (s, 2H), 3.87 (s, 3H), 4.17 (q, J=7.1, 2H), 4.50 (h, J=6.1, 1H), 6.77-6.89 (m. 3H). |
Tags: 60563-13-5 synthesis path| 60563-13-5 SDS| 60563-13-5 COA| 60563-13-5 purity| 60563-13-5 application| 60563-13-5 NMR| 60563-13-5 COA| 60563-13-5 structure
[ 15964-79-1 ]
Methyl 2-(3,4-dimethoxyphenyl)acetate
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[ 6836-21-1 ]
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