Structure of 13214-64-7
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
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CAS No. : | 13214-64-7 |
Formula : | C10H11NO4 |
M.W : | 209.20 |
SMILES Code : | COC1=CC=C(C=C1)C(=O)NCC(O)=O |
MDL No. : | MFCD00181815 |
InChI Key : | SIEIOUWSTGWJGE-UHFFFAOYSA-N |
Pubchem ID : | 128847 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 15 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.2 |
Num. rotatable bonds | 5 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 52.51 |
TPSA ? Topological Polar Surface Area: Calculated from |
75.63 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.5 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-0.24 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.51 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.58 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.71 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.61 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.95 |
Solubility | 23.4 mg/ml ; 0.112 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-0.89 |
Solubility | 26.9 mg/ml ; 0.129 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.31 |
Solubility | 1.02 mg/ml ; 0.00489 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-7.75 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
0.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.56 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.26 |
* 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 |
---|---|---|
With sodium hydroxide; In 1,4-dioxane; water; at 4℃; for 20.75h; | 4.1 N-(4-Methoxybenzoyl)glycine 2.93 g (39 mmol) of glycine dissolved in 41 ml of aqueous 1N sodium hydroxide solution are placed in a 250 ml round-bottomed flask, the mixture is cooled to 4° C., 41 ml of aqueous 1N sodium hydroxide solution and a solution of 7 g (0.041 mol) of 4-methoxybenzoyl chloride in 10 ml of dioxane are added simultaneously, dropwise over 45 minutes, and the mixture is stirred for 20 hours. Concentrated aqueous hydrochloric acid solution is added to pH 1 and the precipitate formed is collected by filtration and recrystallized from isopropyl alcohol. 3.74 g of product are obtained. Melting point: 173° C. | |
With sodium hydroxide; for 0.5h; | General procedure: Glycine (5.0 g, 66.7 mmol) was dissolved in 50 mL of 10percent NaOH solution. BzCl (10.79 mL, 93.0 mmol) was added to the solution and stirred vigorously for 30 min. Crushed ice (60 g) was added to the solution and then concentrated HCl was added dropwise until the mixture was acidified (pH 2-3). The precipitate was filtrated and washed with distilled water until neutrality. The product 2-benzamidoacetic acid was obtained after drying in vacuum. | |
With sodium hydroxide; | General procedure: Glycine (133.0 mmol) wasdissolved in 10percent sodium hydroxide solution (100mL),and then benzoyl chloride (186.0 mmol) was added in portions tothis solution, stirred vigorously after each addition. Crushedice (100 g)was added to the solution and then concentrated HClwas added dropwise until the mixture was acidified (pH2-3). The resulting compounds1a-1g were obtained as whitecrystalline solid. All spectroscopic data of 1a-g[1-3]are in good agreement with the literature reported data |
With sodium hydroxide; at 20℃; for 4h; | Add 10 mL of 10percent NaOH solution to a 50 mL three-necked flask, add 0.75 g of glycine to dissolve, slowly add 1.71 g of 4-methoxybenzoyl chloride dropwise, stir at room temperature for 4 h, adjust the pH to 1-2 with hydrochloric acid, and precipitate a white solid. Tetrahydrofuran: Toluene = 2:1 recrystallization purification to carry out the next condensation reaction.1.0 mmol of the compound VII, 1.0 mmol of the prepared carboxylic acid in 20 mL of CH 2 Cl 2 , the temperature was controlled at about 0 ° C, and 1.2 mmol of EDCI, 2.0 mmol of DIPEA, 1.2 mmol of HOBt were added in sequence, and the reaction was stirred at room temperature overnight. After washing with 10 mL of a 5percent HCl solution, 10 mL of a 5percent NaHCO 3 solution, and 10 mL of a saturated brine, the mixture was dried over anhydrous Na 2 SO 4 and then evaporated to dryness. White solid, yield 58percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With diisopropyl-carbodiimide; In dichloromethane; at 0℃; for 1h;Inert atmosphere; | General procedure: A solution of 1 (0.5 mmol) in CH2Cl2 (5 mL) in a round-bottom flask (25 mL) was cooled with ice-water, and then DIC (0.55 mmol) was added by a syringe. After the resultant mixture was stirred at 0 °C for 1 h, CH2Cl2 was removed by sparging N2 followed by adding 3a (0.55 mmol) or 3b (0.6 mmol) and toluene (10 mL). After refluxing for 3 h, the reaction mixture was diluted with EtOAc (6 mL), passed through a silica gel column, and then evaporated. The product 5a or 5b was isolated from the residue by preparative TLC (silica gel, EtOAc/PE 1/2-1/1, v/v). | |
With acetic anhydride;Heating; | General procedure: A mixture of benzoyl glycines 1a?1d (0.02 mol) and 75 cm3 acetic anhydride was gently heated until a clear solution 2a?2d was obtained. The resulting solution(A) was cooled in an ice bath before treating with a solution (B) of naphthalene diazonium chloride prepared as follows: 3.2 g 1-naphthylamine (0.02 mol) was mixed with 5 cm3 H2O and 6 cm3 conc. HCl. The mixture was cooled in an ice bath and an aqueous solution of 1.38 g NaNO2(0.02 mol) was introduced dropwise and the resulting mixture was stirred for further 30 min. Freshly prepared crude solution (A) was added dropwise in the presence of 1.64 g anhydrous sodium acetate (0.02 mol) and the stirring was continued for further 2 h at 0 C. The resulting crude precipitate was filtered, washed with water, and dried |