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CAS No. : | 1906-82-7 | MDL No. : | MFCD00009173 |
Formula : | C6H11NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | AMBDTBHJFINMSE-UHFFFAOYSA-N |
M.W : | 145.16 | Pubchem ID : | 74702 |
Synonyms : |
Ethyl acetylglycinate
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.67 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 35.24 |
TPSA : | 55.4 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.43 cm/s |
Log Po/w (iLOGP) : | 1.58 |
Log Po/w (XLOGP3) : | -0.34 |
Log Po/w (WLOGP) : | -0.31 |
Log Po/w (MLOGP) : | -0.16 |
Log Po/w (SILICOS-IT) : | 0.06 |
Consensus Log Po/w : | 0.17 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.2 |
Solubility : | 92.5 mg/ml ; 0.637 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.36 |
Solubility : | 63.1 mg/ml ; 0.435 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.13 |
Solubility : | 10.7 mg/ml ; 0.074 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.4 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-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 |
---|---|---|
26% | With thionyl chloride; In benzene; for 1h;Reflux; | A solution of Intermediate 39 (1.2 g) and thionyl chloride (3.2 ml) in anhydrous benzene (10 ml) was heated under reflux for 1 h. The cooled mixture was concentrated under vacuum. The residue obtained was purified by column chromatography on silica gel using hexane/EtOAc 9:1 as eluent to give 500 mg (26%) of the title compound. 1H-NMR (delta, ppm, CDCl3): 4.48 (q, 2H), 1.43 (t, 3H). [ES MS] m/z 226 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | In xylene; for 18h;Heating / reflux; | Example 3 (6.1 g, 0.025 mole) and <strong>[1906-82-7]ethyl acetamidoacetate</strong> (3.62 g, 0.025 mole) are added to 75 mL of xylene and heated to reflux. The solution is refluxed for 18 hours and then the xylene is removed by distillation. The remaining orange residue is recrystallized from methylene chloride and dried to constant weight in a vacuum oven. The title compound is obtained (2.41 g, 28 % yield) as a white crystalline solid with a melting point of 77-80 C whose structure is consistent with HNMR. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With acetic anhydride; In pyridine; | a. Ethyl N-acetyl-glycinate 31 gm of acetic acid anhydride were slowly added to a solution of ethyl glycinate (prepared from 31 gm ethyl glycinate hydrochloride in ether and sodium hydroxide) in 70 ml of pyridine, while stirring and cooling the solution. The resulting mixture was then stirred for one hour at room temperature and subsequently evaporated, yielding 15 gm (55% of theory) of ethyl N-acetyl-glycinate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | A methylene chloride solution (5.0 ml) of N-acetylglycine ethyl ester (72.5 mg, 0.50 mmol) and N-methylimidazole (50.4 mg, 0.61 mmol) was cooled to -45C, and a methylene chloride solution (0.5 ml) of palmitoyl chloride (142.6 mg, 0.50 mmol) was added thereto in nitrogen atmosphere. After the mixture was stirred for 20 minutes at the same temperature, a methylene chloride solution (0.5 ml) of titanium tetrachloride (340.4 mg, 1.78 mmol) and a methylene chloride solution (0.5 ml) of tributylamine (372.4 mg, 2.01 mmol) were added thereto. The resulting mixture was stirred for 2 hours at -45C. Water was added thereto, and the mixture was heated to room temperature, and the organic layer was separated. Further, the water layer was extracted twice with methylene chloride, and the organic layers were combined and dried with magnesium sulfate. After the solvent was removed in reduced pressure, the obtained crude product was purified by silica gel chromatography (Kieselgel 60 manufactured by Merck, hexane : ethyl acetate = 3 : 2) to obtain the title compound (148.8 mg, yield: 88%). 1H NMR (400MHz, CDCl3 / ppm): delta0.88(t, 3H), 1.25-1.36 (m, 29H), 2.07(s, 3H), 2.71(m, 2H), 4.26(q, 2H), 5.23(d, 1H), 6.62(d, 1H) | |
84% | A chlorobenzene solution (45.0 ml) of N-acetylglycine ethyl ester (1.50 g, 10.33 mmol) and N-methylimidazole (1.02 g, 12.40 mmol) was cooled to -10C, and palmitoyl chloride (2.84 g, 10.33 mmol) was added thereto in nitrogen atmosphere. After the mixture was stirred for 45 minutes at the same temperature, titanium tetrachloride (6.86 mg, 36.16 mmol) and tributylamine (7.66g, 41.32 mmol) were added thereto. The resulting mixture was stirred for 2 hours at -10C. Water (20 mL) was added thereto, and the mixture was heated to room temperature, and the organic layer was separated. It was confirmed by comparative analysis with sample product using HPLC that the organic layer contained 3.33 g of the title compound (yield: 84%). | |
74 - 80% | Example 4: Production of ethyl 2-acetylamino-3-oxooctadecanoate A chlorobenzene solution (45.0 ml) of N-acetylglycine ethyl ester (1.50 g, 10.33 mmol) and N-methylimidazole (1.02 g, 12.40 mmol) was cooled to -20C, and palmitoyl chloride (2.84 g, 10.33 mmol) was added thereto in nitrogen atmosphere. After the mixture was stirred for 45 minutes at the same temperature, titanium tetrachloride (6.86 mg, 36.16 mmol) and triethylamine (4.18 g, 41.31 mmol) were added thereto. The resulting mixture was stirred for 2 hours at -20C. Water (20 mL) was added thereto, and the mixture was heated to room temperature, and the organic layer was separated. It was confirmed by comparative analysis with sample product using HPLC that the organic layer contained 2.92 g of the title compound (yield: 74%).; Example 5: Production of ethyl 2-acetylamino-3-oxooctadecanoate A chlorobenzene solution (45.0 ml) of N-acetylglycine ethyl ester (1.50 g, 10.33 mmol) and N-methylimidazole (1.02 g, 12.40 mmol) was cooled to -10C, and palmitoyl chloride (2.84 g, 10.33 mmol) was added thereto in nitrogen atmosphere. After the mixture was stirred for 45 minutes at the same temperature, titanium tetrachloride (6.86 mg, 36.16 mmol) and triethylamine (4.18 g, 41.31 mmol) were added thereto. The resulting mixture was stirred for 2 hours at -10C. Water (20 mL) was added thereto, and the mixture was heated to room temperature, and the organic layer was separated. It was confirmed by comparative analysis with sample product using HPLC that the organic layer contained 2.92 g of the title compound (yield: 80%).; Example 7: Production of ethyl 2-acetylamino-3-oxooctadecanoate A chlorobenzene solution (45.0 ml) of N-acetylglycine ethyl ester (1.50 g, 10.33 mmol) and N-methylimidazole (1.02 g, 12.40 mmol) was cooled to 0C, and palmitoyl chloride (2.84 g, 10.33 mmol) was added thereto in nitrogen atmosphere. After the mixture was stirred for 25 minutes at the same temperature, titanium tetrachloride (6.86 mg, 36.16 mmol) and triethylamine (4.18 g, 41.31 mmol) were added thereto. The resulting mixture was stirred for 2 hours at 0C. Water (20 mL) was added thereto, and the mixture was heated to room temperature, and the organic layer was separated. It was confirmed by comparative analysis with sample product using HPLC that the organic layer contained 2.93 g of the title compound (yield: 74%). |
71% | A dichloromethane solution (45.0 ml) of N-acetylglycine ethyl ester (1.50 g, 10.33 mmol) and N-methylimidazole (1.02 mg, 12.40 mmol) was cooled to -45C, and palmitoyl chloride (2.84 g, 10.33 mmol) was added thereto in nitrogen atmosphere. After the mixture was stirred for 20 minutes at the same temperature, titanium tetrachloride (6.86 mg, 36.16 mmol) and triethylamine (4.18 g, 41.31 mmol) were added thereto. The resulting mixture was stirred for 2 hours at -45C. Water (20 mL) was added thereto, and the mixture was heated to room temperature, and the organic layer was separated. It was confirmed by comparative analysis with sample product using HPLC that the organic layer contained 2.81 g of the title compound (yield: 71%). | |
66% | A toluene solution (33.0 ml) of N-acetylglycine ethyl ester (1.00 g, 6.89 mmol) and N-methylimidazole (679 mg, 8.27 mmol) was cooled to -20C, and palmitoyl chloride (1.89 g, 6.89 mmol) was added thereto in nitrogen atmosphere. After the mixture was stirred for 30 minutes at the same temperature, titanium tetrachloride (4.57 mg, 24.12 mmol) and triethylamine (2.79 g, 27.56 mmol) were added thereto. The resulting mixture was stirred for 2 hours at -20C. Water (20 mL) was added thereto, and the mixture was heated to room temperature, and the organic layer was separated. It was confirmed by comparative analysis with sample product using HPLC that the organic layer contained 1.75 g of the title compound (yield: 66%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In two necked RB flask equipped with watercondenser sodium hydride (0.55 g, 13.79 mmole) was slowly added in portion toan ice cooled solution of 3a, acetylamino-acetic acid ethyl ester (1.0g, 6.89 mmole), 18-Crown 6-ether (1 eq.) and ethylformate (1.06 mL, 13.79 mmole)in dry toluene. The reaction mixture was then gradually warmed to roomtemperature and heated to 60 C for 1h to sluggishness. Upon completion,the reaction mixture was cooled to rt and excess of sodium hydride quenchedwith ethanol. The resultant mixture was acidified to pH 4.0 using 2 N HCl and stirred at 65 C for 2 h. Uponcompletion the reaction mixture cooled to rt, basified using sat.NaHCO3,extracted with ethyl acetate. The organiclayer dried over anhydrous sodium sulfate (Na2SO4) and evaporatedunder vacuo to afford pure white solid product (72%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With 1-methyl-1H-imidazole; tributyl-amine; titanium tetrachloride; In dichloromethane; at -45℃; for 0.5h; | A solution of ethyl N-acetylglycinate (98%, 7.41 g, 50.0 mmol) and 1-methyl-1H-imidazole (99%, 4.81 mL, 60.0 mmol) in dichloromethane (100 mL) was cooled to -45 C. and treated with 2-methylbenzoyl chloride (99%, 6.59 mL, 50.0 mmol). The reaction was stirred at -45 C. for 10 minutes. Titanium(IV) chloride (19.2 mL, 175 mmol) was added, followed by tri-n-butylamine (98%, 48.6 mL, 200 mmol), and stirring was continued at the same temperature for 30 minutes. The reaction was quenched with water and extracted with diethyl ether; the combined organic layers were washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated in vacuo. Silica gel chromatography (Eluents: 1:5 ethyl acetate/heptane followed by 1:2 ethyl acetate/heptane) afforded the product. Yield: 6.00 g, 22.8 mmol, 46%. APCI m/z 264.1 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 7.93 (dd, J=7.8, 1.2 Hz, 1H), 7.44 (ddd, J=7.6, 7.5, 1.4 Hz, 1H), 7.26-7.34 (m, 2H), 6.89 (br d, J=7 Hz, 1H), 6.05 (d, J=7.2 Hz, 1H), 4.04-4.19 (m, 2H), 2.45 (br s, 3H), 2.11 (s, 3H), 1.06 (t, J=7.1 Hz, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; | A mixture of8.07 g (56 mmol) of N-acetylglycine N',N'-dimethylamide (obtained in 94%yield from N-acetylglycine ethyl ester and excess 40% aqueous dimethylamine10),trimethylchlorosilane (12.1 g, 112 mmol) and NEt3 (70 ml) wasrefluxed for 4 h and allowed to cool down to ambient temperature. Thesolids formed were filtered off, the solvent was removed in vacuo and theremaining oil was distilled. Yield 8.20 g (68%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium ethanolate; formic acid ethyl ester; In toluene; at 0℃; for 0.333333h; | The 50 ml of toluene sodium ethoxide with suspended adding dropwisely 11 ml formic acid ethyl ester;After dropping, maintaining the temperature less than 0 C, then 20 minutes containing the dropping 15g toluene solution of acetyl glycine ethyl ester 11 ml.Combined ice water after extracting toluene solution, adding 8g potassium thiocyanate, stirring to dissolve;Filtered to obtain 2-mercapto -1H-imidazole-4-carboxylic acid ethyl ester; |
[ 34597-05-2 ]
Ethyl 2-(N-methylacetamido)acetate
Similarity: 0.91
[ 6290-05-7 ]
Diethyl 2,2'-azanediyldiacetate
Similarity: 0.84
[ 34597-05-2 ]
Ethyl 2-(N-methylacetamido)acetate
Similarity: 0.91
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