Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 13674-16-3 | MDL No. : | MFCD06654233 |
Formula : | C10H12O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 180.20 | Pubchem ID : | - |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.3 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 48.28 |
TPSA : | 46.53 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) : | -6.37 cm/s |
Log Po/w (iLOGP) : | 1.96 |
Log Po/w (XLOGP3) : | 1.45 |
Log Po/w (WLOGP) : | 0.76 |
Log Po/w (MLOGP) : | 1.41 |
Log Po/w (SILICOS-IT) : | 1.6 |
Consensus Log Po/w : | 1.44 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.95 |
Solubility : | 2.03 mg/ml ; 0.0113 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.03 |
Solubility : | 1.67 mg/ml ; 0.00927 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.35 |
Solubility : | 0.803 mg/ml ; 0.00446 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.81 |
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 |
---|---|---|
90% | With sodium hydrogencarbonate; In methanol; | Step 1: 2-Hydroxy-3-phenyl-propionic acid methyl ester. Hydrogen chloride was bubbled for 15 minutes into a solution of 2-hydroxy-3-phenyl-propionic acid (10.0 g, 60 mmol) in 100 mL of methanol at room temperature. The vessel was sealed and then stirred overnight at room temperature. The reaction was made basic by the addition of 5% NaHCO3 and then concentrated under reduced pressure to remove the methanol. The residue was diluted with water and extracted with ethyl acetate. The organic layer was extracted with saturated NaCl, dried (MgSO4) and the solvent removed under reduced pressure to give 2-hydroxy-3-phenyl-propionic acid methyl ester (9.7 g, 90%) as a yellow oil, MS m/z 180 [M]+. Elemental Analysis for C10H12O3 Calc'd: C, 66.65; H, 6.71; N, 0.00 Found: C, 66.52; H, 6.86; N, 0.29 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With sulfuric acid; at 20 - 30℃; | 2-hydroxy-3-phenylpropanoic acid (9A) (5 g, 30.1 mmol) was dissolved in methanol (100 mL), concentrated sulfuric acid (1 mL) was added thereto, and the reaction was allowed to proceed at 30 C. overnight. The reaction solution was concentrated, then dissolved with ethyl acetate (50 ml), washed once with saturated sodium bicarbonate (50 ml) and then once with saturated sodium chloride (50 ml), dried over anhydrous sodium sulfate, and concentrated to give methyl 2-hydroxy-3-phenylpropanonate (9B) as a white solid (6 g, 100%). 1H NMR (400 MHz, DMSO) delta 7.30-7.23 (m, 2H), 7.23-7.15 (m, 3H), 5.53 (d, 1H). 4.27-4.22 (m, 1H), 3.60 (s, 3H), 2.95 (dd, 1H), 2.82 (dd, 1H). |
98% | With hydrogenchloride; at 20℃; for 9.33333h; | Step 1: Hydrochloric acid gas was bubbled into a solution of 2-hydroxy-3-phenyl-propionic acid (6.0 g, 36.10 mmol) in MeOH (250 ml) at room temperature under CaSO4 tube for 20 minutes. The resulting colorless solution was stirred for 7 hours and concentrated in vacuo to afford 2-hydroxy-3-phenyl-propionic acid methyl ester as a brown syrup (6.36 g, 98% yield): MS (ESI) m/z 181. |
90% | With hydrogenchloride; at 20℃; | [0127] Example 8: Synthesis of 2-[(3-bromo-4'-[[(2-butyl-1-benzofuran-3- yl) carbonyl] (methyl) amino] methyl}-l, L -BIPHENYL-4-YL) OXY]-3-PHENYLPROPANOIC ACID.; [0128] Step 1: 2-Hydroxy-3-phenyl-propionic acid methyl ester. Hydrogen chloride was bubbled for 15 minutes into a solution of 2-hydroxy-3-phenyl-propionic acid (LO. OG, 60 mmol) in 100 ML of methanol at room temperature. The vessel was sealed and then stirred overnight at room temperature. The reaction was made basic by the addition of 5% NAHCO3 and then concentrated under reduced pressure to remove the methanol. The residue was diluted with water and extracted with ethyl acetate. The organic layer was extracted with saturated NaCI, dried (MGS04) and the solvent removed under reduced pressure to give 2-hydroxy-3-phenyl- propionic acid methyl ester (9.7g, 90%) as a yellow oil, MS M/Z 180 [M] +. Elemental Analysis FOR CLOHL203. Calc'd: C, 66.65 ; H, 6.71 ; N, 0.00. Found: C, 66.52 ; H, 6.86 ;. N, 0.29 |
90% | With hydrogenchloride; at 20℃; | Phenyltrimethylammoniun tribromide (9.45 g, 25.1 mmol) was added under nitrogen in portions over approximately 2 h to a solution of 1-(6-methoxy-naphthalen-2-yl)-ethanone (5.05 g, 25.2 mmol) in 50 mL of anhydrous THF at room temperature. After the addition the reaction was stirred at room temperature for 0.5 h. and then 250 mL of cold water was added. The solid present was collected by filtration, rinsed with 50 mL of water and dried under reduced pressure to give 6.66 g of a tan solid. Recrystallization of the solid from isopropyl alcohol gave 2-bromo-1-(6-methoxy-2-naphthyl)ethanone (4.07 g, 58%) as a brown solid, mp 109-112 C. Elemental Analysis for C13H11BrO2Calc'd: C, 55.94; H, 3.97; N, 0.00. Found: C, 56.03; H, 3.94; N, 0.00. Step 2: 4-(6-methoxy-2-naphthyl)-2-phenyl-1,3-thiazole. Thiobenzamide (447 mg, 3.26 mmol) was added under nitrogen to a solution of (2-bromo-1-(6-methoxy-2-naphthyl)ethanone (906 mg, 3.25 mmol), prepared in the previous step, in 25 mL of absolute ethanol at approximately 70 C. After the addition the reaction was refluxed for 2 h. The solid was collected by filtration, rinsed with absolute ethanol and dried under reduced pressure to give 4-(6-methoxy-2-naphthyl)-2-phenyl-1,3-thiazole (909 mg, 88%) as a white solid, mp 191-193 C. Elemental Analysis for C20H15NOS Calc'd: C, 75.68; H, 4.76; N, 4.41. Found: C, 75.37; H, 4.65; N, 4.31. Step 3: 6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthol. A solution of 4-(6-methoxy-2-naphthyl)-2-phenyl-1,3-thiazole (804 mg, 2.53 mmol), prepared in the previous step, in 50 mL of glacial HOAc plus 25 mL of 48% HBr was stirred under nitrogen at 120 C. for 3 h. The solvent was removed under reduced pressure and the residue partitioned between 10% methanol-methylene chloride and 5% NaHCO3. (Note: The solid that did not dissolve in either layer was collected by filtration and saved as the HCL salt of the desired product). The aqueous layer was separated and extracted three times with 10% methanol-methylene chloride. The combined extracts were dried (MgSO4), filtered and the solvent removed under reduced pressure to give 6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthol (650 mg, 85%) as a brown solid, mp 194-197 C. Elemental Analysis for C19H13NOS Calc'd: C, 75.22; H, 4.32; N, 4.62. Found: C, 74.22; H, 4.12; N, 4.43 Step 4: 2-Hydroxy-3-phenyl-propionic acid methyl ester. Hydrogen chloride was bubbled for 15 minutes into a solution of 2-hydroxy-3-phenyl-propionic acid (10.0 g, 60 mmol) in 100 mL of methanol at room temperature. The vessel was sealed and then stirred overnight at room temperature. The reaction was made basic by the addition of 5% NaHCO3 and then concentrated under reduced pressure to remove the methanol. The residue was diluted with water and extracted with ethyl acetate. The organic layer was extracted with saturated NaCl, dried (MgSO4), filtered and the solvent removed under reduced pressure to give 2-hydroxy-3-phenyl-propionic acid methyl ester (9.7 g, 90%) as a yellow oil, MS m/z 180 [M]+. Elemental Analysis for C10H12O3 Calc'd: C, 66.65; H, 6.71; N, 0.00. Found: C, 66.52; H, 6.86; N, 0.29 Step 5: 3-Phenyl-2-trifluoromethanesulfonyloxy-propionic acid methyl ester. Triethylamine (931 muL, 6.68 mmol) was added under nitrogen to a solution of 2-hydroxy-3-phenyl-propionic acid methyl ester (1.00 g, 5.57 mmol), prepared in the previous step, in 20 mL of chloroform (99.9%; free of ethanol) at dry ice-acetone temperature. Trifluoromethanesulfonic anhydride (1.03 mL, 6.13 mmol) was then added dropwise over 15 minutes. The cooling bath was removed and the reaction was stirred overnight at room temperature. The reaction was extracted with 1 N HCl, 5% NaHCO3, dried (MgSO4), filtered and the solvent removed under reduced pressure to give 1.53 g a brown oil. Purification of the oil on 100 g of silica gel (230-400 mesh) using 3:1 methylene chloride:hexane as the eluent gave 3-phenyl-2-trifluoromethanesulfonyloxy-propionic acid methyl ester (1.106 g, 64%) as clear oil. Elemental Analysis for C11H11F3O5S Calc'd: C, 42.31; H, 3.55; N, 0.00. Found: C, 42.15; H, 3.35; N, 0.14 Step 6: Methyl 3-phenyl-2-[6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthyl]oxy} propanoate. A mixture of 6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthol (247 mg, 0.814 mmol), prepared in step 3,3-phenyl-2-trifluoromethanesulfonyloxy-propionic acid methyl ester (387 mg, 1.24 mmol), prepared in the previous step, and cesium carbonate (532 mg, 1.63 mmol) in 20 mL of acetone was stirred under nitrogen at room temperature for 17 h. The reaction was concentrated under reduced pressure to remove the acetone. The residue was partitioned between methylene chloride and water. The aqueous layer was separated and extracted three times with methylene chloride. The combined extracts were dried (MgSO4), filtered and the solvent removed under reduced pressure to give 449 mg of a brown oil. Purification of the oil on 300 g of silica gel (230-400 mesh) using 1:1 to 3:2 methylene chloride:hexane as the eluent gave methyl 3-phenyl-2... |
With toluene-4-sulfonic acid; In toluene; for 2h;Reflux; | General procedure: A mixture of mandelic acid(12 mmol), alcohol (1.5 eq) , TsOH (500 mg) and toluene(20mL) wasrefluxed for 2 h. The resultant mixture was diluted with NaHCO3(sat.aq.)(3X10mL) and water( 2X10mL) and dried over Na2SO4.Flash chromatography on silica gel (eluent: ethyl acetate/petroleum ether =6:1) gave the correspondingracemic mandelate ester. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With caesium carbonate; In N-methyl-acetamide; water; | EXAMPLE 5 Methyl L-3-phenyllactate L-3-Phenyllactic acid (5 g, 30 mmol) was dissolved in 25 mL of dimethylformamide and cesium carbonate (9.94 g, 30.5 mmol) was added. After the evolution of gas ceased, methyl iodide (8.52 g, 60 mmol) was added and the mixture was stirred for 18 hours at room temperature. Water was then added and the mixture extracted with ethyl acetate. The organic phase was separated, washed with water, dried over magnesium sulfate, and the solvent removed in vacuo to give the title compound as a colorless oil (5.4 g, 100% yield). Anal. calcd for C10 H12 O3: C, 66.65; H, 6.71. Found: C, 66.62; H, 6.69. |
With caesium carbonate; In N-methyl-acetamide; water; | EXAMPLE 12 Methyl L-3-phenyllactate L-3-Phenyllactic acid (5 g, 30 mmol) was dissolved in 25 mL of dimethylformamide and cesium carbonate (9.94 g, 30.5 mmol) was added. After the evolution of gas ceased, methyl iodide (8.52 g, 60 mmol) was added and the mixture was stirred for 18 hours at room temperature. Water was then added and the mixture extracted with ethyl acetate. The organic phase was separated, washed with water, dried over magnesium sulfate, and the solvent removed in vacuo to give the title compound as a colorless oil (5.4 g, 100% yield). Anal. calcd for C10 H12 O3: C, 66.65; H, 6.71. Found: C, 66.62; H, 6.69. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; di-isopropyl azodicarboxylate; triphenylphosphine; In benzene; at 20℃; for 0.5h; | 2-{4'-[5-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-yl]-biphenyl-4-yloxy}-3-phenyl-propionic Acid Diisopropyl azodicarboxylate (0.42 mL, 2.52 mmol) in benzene (10 mL) was added dropwise into a cold (0 C.) mixture of 4'-[5-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-yl]-biphenyl-4-ol (0.5 g, 1.26 mmol), 3-phenyllactic acid methyl ester (0.45 g, 2.52 mmol), triphenylphosphine (0.66 g, 2.52 mmol), and benzene (20 mL). The reaction mixture was stirred at room temperature for 30 minutes, poured into water, and extracted with ethyl ether. The organic extracts were dried over MgSO4. Evaporation gave a yellow oil (0.6 g). This residue was taken in methyl alcohol (15 mL) and tetrahydrofuran (15 mL) and treated with sodium hydroxide (2 N, 3.0 mL). The reaction mixture was stirred for 30 minutes, poured into water, acidified with HCl (2 N), and extracted with ethyl ether. The organic extracts were dried over MgSO4. Evaporation and crystallization from ethyl ether/hexanes gave a white solid (0.38 g, 55% yield): mp 183-184; MS m/e 544 (M+H)+; Analysis for: C32H24F3NO4Calc'd: C, 70.71; H, 4.45; N, 2.58 Found: C, 70.50; H, 4.32; N, 2.53. |
[ 4358-87-6 ]
Methyl 2-hydroxy-2-phenylacetate
Similarity: 0.87
[ 20698-91-3 ]
(R)-Methyl 2-hydroxy-2-phenylacetate
Similarity: 0.87
[ 21210-43-5 ]
(S)-Methyl 2-hydroxy-2-phenylacetate
Similarity: 0.87
[ 7326-19-4 ]
(R)-2-Hydroxy-3-phenylpropanoic acid
Similarity: 0.85
[ 4358-87-6 ]
Methyl 2-hydroxy-2-phenylacetate
Similarity: 0.87
[ 20698-91-3 ]
(R)-Methyl 2-hydroxy-2-phenylacetate
Similarity: 0.87
[ 21210-43-5 ]
(S)-Methyl 2-hydroxy-2-phenylacetate
Similarity: 0.87
[ 7326-19-4 ]
(R)-2-Hydroxy-3-phenylpropanoic acid
Similarity: 0.85
[ 4358-87-6 ]
Methyl 2-hydroxy-2-phenylacetate
Similarity: 0.87
[ 20698-91-3 ]
(R)-Methyl 2-hydroxy-2-phenylacetate
Similarity: 0.87
[ 21210-43-5 ]
(S)-Methyl 2-hydroxy-2-phenylacetate
Similarity: 0.87
[ 1508892-33-8 ]
Methyl 2-hydroxy-3-(3-hydroxyphenyl)propanoate
Similarity: 0.84
[ 97415-09-3 ]
(R)-Benzyl 2-hydroxy-2-phenylacetate
Similarity: 0.82