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| | Diethyl acetamidomalonate Basic information |
| | Diethyl acetamidomalonate Chemical Properties |
| Melting point | 95-98 °C (lit.) | | Boiling point | 185 °C/20 mmHg (lit.) | | density | 1.2850 (rough estimate) | | refractive index | 1.4640 (estimate) | | Fp | 185°C/20mm | | storage temp. | Sealed in dry,Room Temperature | | solubility | Chloroform (Slightly), Methanol (Slightly) | | pka | 11.93±0.59(Predicted) | | form | Crystalline Powder | | color | White to light yellow | | Water Solubility | Soluble in chloroform and methanol. Slightly soluble in water. | | BRN | 783883 | | InChI | 1S/C9H15NO5/c1-4-14-8(12)7(10-6(3)11)9(13)15-5-2/h7H,4-5H2,1-3H3,(H,10,11) | | InChIKey | ISOLMABRZPQKOV-UHFFFAOYSA-N | | SMILES | CCOC(=O)C(NC(C)=O)C(=O)OCC | | CAS DataBase Reference | 1068-90-2(CAS DataBase Reference) | | NIST Chemistry Reference | Propanedioic acid, (acetylamino)-, diethyl ester(1068-90-2) | | EPA Substance Registry System | Propanedioic acid, 2-(acetylamino)-, 1,3-diethyl ester (1068-90-2) |
| | Diethyl acetamidomalonate Usage And Synthesis |
| Chemical Properties | white to light yellow crystalline powder | | Uses |
Diethyl acetamidomalonate is a versatile building block used for the synthesis of various pharmaceutical and biologically active compounds. It is an intermediate for the preparation of Novobiocin analogues as potential heat shock protein 90 inhibitors. It is also used as a important intermediates in syntheses of vitamins B1 and B6, barbiturates, non-steroidal anti-inflammatory agents, other numerous pharmaceuticals.
| | Chemical Reactivity | Diethyl acetamidomalonate is flammable; upon heating it decomposes releasing toxic nitrogen oxide fumes.
| | Safety Profile | An eye irritant. When heated todecomposition it emits toxic fumes of NOx. | | Synthesis | Diethyl 2-aminomalonate hydrochloride (1.69 g, 8.0 mmol) and triethylamine (3.4 mL, 24 mmol, 3.0 eq.) were dissolved in dichloromethane (120 mL) at 0 °C. Acetyl chloride (0.57 mL, 8.0 mmol, 1.0 eq.) was added slowly and dropwise with stirring and the reaction mixture was gradually warmed to room temperature and stirred overnight. After completion of the reaction, the mixture was diluted with dichloromethane (100 mL) and washed sequentially with 1 M hydrochloric acid (3 x 60 mL). The aqueous phase was then back-extracted with dichloromethane (2 x 60 mL), the organic layers were combined and dried over anhydrous magnesium sulfate. The solvent was removed by concentration under reduced pressure to give a pure white solid product. Yield: 1.68 g (96% yield). The product was characterized as follows: melting point 96 °C (literature value 97 °C); 1H NMR (300 MHz, CDCl3) δ [ppm]: 1.30 (t, J=7.1Hz, 6H, 7-CH3,9-CH3), 2.08 (s, 3H, 5-CH3), 4.27 (m, 4H, 6-CH2,8-CH2), 5.18 (d, J=7.1Hz, 1H), 5.18 (d, J=7.1Hz, 1H). 7.1 Hz, 1H, 2-CH), 6.67 (d, J=5.7 Hz, 1H, 2-NH); 13C NMR (75 MHz, CDCl3) δ [ppm]: 14.0 (q, C-7, C-9), 22.8 (q, C-5), 56.5 (d, C-2), 62.6 (t, C-6, C-8), 166.5 (s, C -1, C-3), 169.9 (s, C-4); high-resolution mass spectrometry (ESI+): 240.0842 calculated value for C9H15N5O+Na+, 240.0824 measured value. | | Purification Methods | Crystallise the ester from *benzene/pet ether. [Beilstein 4 III 2993.] | | References | [1] Patent: WO2013/26765, 2013, A1. Location in patent: Page/Page column 15-16
[2] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 5, p. 1011 - 1026 |
| | Diethyl acetamidomalonate Preparation Products And Raw materials |
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