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| | 3-Amino-2-butenoic acid ethyl ester Basic information |
| Product Name: | 3-Amino-2-butenoic acid ethyl ester | | Synonyms: | Ethyl (2E)-3-amino-2-butenoate;ETHYL 3-AMINO-2-BUTENOATE;ETHYL (2E)-3-AMINOBUT-2-ENOATE;ETHYL BETA-AMINOCROTONATE;ETHYL B-IMINOBUTYRATE;β-Aminocrotonic acid, ethyl ester;Ethyl 3-aminocrotonate, 98.50%;3-AMINO-2-BUTENOIC ACID ETHYL ESTER | | CAS: | 7318-00-5 | | MF: | C6H11NO2 | | MW: | 129.16 | | EINECS: | 230-782-0 | | Product Categories: | API intermediates | | Mol File: | 7318-00-5.mol |  |
| | 3-Amino-2-butenoic acid ethyl ester Chemical Properties |
| Melting point | 33-35 °C(lit.) | | Boiling point | 210-215 °C(lit.) | | density | 1.022 g/mL at 25 °C(lit.) | | refractive index | 1.5-1.502 | | Fp | 207 °F | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | soluble in Chloroform, Methanol | | form | Low Melting Solid or Liquid | | pka | 5.32±0.70(Predicted) | | color | Slightly yellow | | InChI | InChI=1S/C6H11NO2/c1-3-9-6(8)4-5(2)7/h4H,3,7H2,1-2H3 | | InChIKey | YPMPTULBFPFSEQ-UHFFFAOYSA-N | | SMILES | C(OCC)(=O)C=C(N)C | | CAS DataBase Reference | 7318-00-5(CAS DataBase Reference) | | NIST Chemistry Reference | 2-Butenoic acid, 3-amino-, ethyl ester(7318-00-5) |
| | 3-Amino-2-butenoic acid ethyl ester Usage And Synthesis |
| Chemical Properties | Slightly yellow low melting solid or liquid | | Uses | Ethyl 3-Aminocrotonate is used as a reagent to synthesize Nitrendipine (N490150), a calcium channel antagonist that is used to treat patients with hypertension. Ethyl 3-Aminocrotonate is also used as a reagent to synthesize (S)-Felodipine (F232370), a calcium entry blocker that has antihypertensive properties. | | Synthesis | General procedure for the synthesis of ethyl 3-aminocrotonate from ethyl acetoacetate: β-keto ester (1.0 eq.), ammonium acetate (3.0 eq.), and acetic acid (dropwise) were dissolved in dry toluene (6 mL) in a 10 mL reaction glass vial containing a stirring magnet and a molecular sieve. The vial was tightly sealed with an Aluminum-Teflon convoluted cap and the mixture was microwaved at 140 °C for 20 min at 60 W power. After completion of the reaction, it was cooled to 50 °C by gas injection. The crude reaction mixture was partitioned between ethyl acetate (15 mL) and saturated sodium bicarbonate solution (15 mL), and the aqueous layer was extracted with ethyl acetate (3 x 15 mL). The organic layers were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by rapid chromatography on silica gel.Synthesis of ethyl 3-aminobut-2-enoate (6a): ethyl 3-(2-fluorophenyl)-3-oxopropanoate 5a (1.0 eq.), ammonium acetate (4.0 eq.), and acetic acid (7 drops) were reacted under the above conditions. Rapid chromatographic purification using hexane/ethyl acetate (80:20 to 70:30) as eluent gave an analytically pure product in 89% yield.1H NMR (CDCl3, 300 MHz) δ (ppm): 1.24 (t, 3H, J=7.36 Hz), 3.51 (s, 3H), 4.09 (q, 2H, J=7.28 Hz). 4.60 (s, 1H). | | References | [1] Comptes Rendus Chimie, 2011, vol. 14, # 5, p. 511 - 515
[2] Patent: WO2012/147103, 2012, A2. Location in patent: Page/Page column 7
[3] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1986, vol. 35, p. 1438 - 1442
[4] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1986, # 7, p. 1586 - 1592
[5] European Journal of Medicinal Chemistry, 2018, vol. 155, p. 946 - 960 |
| | 3-Amino-2-butenoic acid ethyl ester Preparation Products And Raw materials |
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