Category: 178388-79-9

Some common heterocyclic compound, 178388-79-9, name is 3-(1H-Imidazol-2-yl)propanoic acid, molecular formula is C6H8N2O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Computed Properties of C6H8N2O2

4.2.1 Methyl 3-(1H-imidazol-2-yl) propanoate To a round bottom flask charged with 143 mL of methanol was added 1 g (g) (1 equiv, 7.15 mmol) of 3-(1H-imidazol-2-yl)propanoic acid (Astatech Inc.). This solution was cooled to 0 C, then 5.2 mL (10 equiv, 71.5 mmol) of thionyl chloride was added and the reaction stirred for 5 h. Upon completion, the reaction was reduced, diluted with dichloromethane, and washed three times with 0.1 M K2CO3. The organic portions were dried with sodium sulfate, filtered, and reduced to afford the HCl salt of methyl 3-(1H-imidazol-2-yl)propanoate as a white powder in quantitative yield (1.35 g, 99%). deltaH (500 MHz, DMSO-d6) 2.98 (s, 2H, CH2CH2Im), 3.16 (s, 2H, CH2CH2Im), 3.59 (s, 3H, CH3), 7.52 (s, 2H, Im), 14.58 (s, 1H, NH); deltaC (125 MHz, DMSO-d6) 20.44, 29.98, 51.45, 118.20, 145.76, 171.31; HRMS (ES+) calcd for [C7H10N2O2+H] 155.08205, found 155.08202.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 178388-79-9, its application will become more common.

Reference:
Article; Cummings, Christopher G.; Hamilton, Andrew D.; Tetrahedron; vol. 69; 5; (2013); p. 1663 – 1668;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 178388-79-9 as follows. Recommanded Product: 178388-79-9

A mixture of compound 5b (128 mg, 0.3 mmol), imidazole-4-propionic acid (1.26 g, 9 mmol; 30 eq.; prepared from urocanic acid by catalytic hydrogenation using 10% Pd-C in acetic acid, following the procedure described in J. Altman, N. Shoef, M. Wilchek, and A. Warshawsky J. Chem. Soc., Perkin Trans. I, 1984, 59), copper powder (38 mg, 0.6 mmol; 2 eq.), potassium carbonate (83 mg, 0.6 mmol; 2 eq.) was flushed with anhydrous nitrogen and heated in a sealed tube at 190-200 C. (oil bath temp.) for 2 h. Upon cooling, to the mixture was added MeOH, and the insoluble material was filtered. The filtrate was concentrated in vacuo and purified by C-18 reverse phase column (YMC, eluting with 15% CH3CN-water containing 0.1% TFA) to obtain 12 mg (0.023 mmol, Y. 7.5%) of the title compound Example 329 as amorphous powder (about 1:1 mixture of two regio-isomers): HPLC purity 96% (AP, at 254 nm); MS (LC/MS) m/z 531 (M+H); 1H NMR (CD3OD) delta ppm 2.74, 3.00 (2H, 2t, J=7 Hz), 2.82, 3.11 (2H, 2t, J=7 Hz), 3.59 (4H, br, CH2N), 3.79 (4H, br, CH2N), 3.79, 4.10 (3H, 2s, CH3O), 6.73 (s), 7.33 (s), 7.48 (5H, br. s, Ar-Hs), 7.93 (br.s), 8.00 (s), 8.10 (s), 8.40 (s), 8.77 (s), 9.43 (br.s).

According to the analysis of related databases, 178388-79-9, the application of this compound in the production field has become more and more popular.

Some common heterocyclic compound, 178388-79-9, name is 3-(1H-Imidazol-2-yl)propanoic acid, molecular formula is C6H8N2O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Application In Synthesis of 3-(1H-Imidazol-2-yl)propanoic acid

4.2.1 Methyl 3-(1H-imidazol-2-yl) propanoate To a round bottom flask charged with 143 mL of methanol was added 1 g (g) (1 equiv, 7.15 mmol) of 3-(1H-imidazol-2-yl)propanoic acid (Astatech Inc.). This solution was cooled to 0 C, then 5.2 mL (10 equiv, 71.5 mmol) of thionyl chloride was added and the reaction stirred for 5 h. Upon completion, the reaction was reduced, diluted with dichloromethane, and washed three times with 0.1 M K2CO3. The organic portions were dried with sodium sulfate, filtered, and reduced to afford the HCl salt of methyl 3-(1H-imidazol-2-yl)propanoate as a white powder in quantitative yield (1.35 g, 99%). deltaH (500 MHz, DMSO-d6) 2.98 (s, 2H, CH2CH2Im), 3.16 (s, 2H, CH2CH2Im), 3.59 (s, 3H, CH3), 7.52 (s, 2H, Im), 14.58 (s, 1H, NH); deltaC (125 MHz, DMSO-d6) 20.44, 29.98, 51.45, 118.20, 145.76, 171.31; HRMS (ES+) calcd for [C7H10N2O2+H] 155.08205, found 155.08202.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 178388-79-9, its application will become more common.