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[(2-ethoxycarbonylethylamino)(2-hydroxyethylamino)methylidene]propanedinittile[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
60%
A mixture of β-alanine ethyl ester hydrochloride (30 g), triethylamine (38 mL), [bis(methylthio)methylidene]propanedinitrile (32 g) and ethanol (310 mL) was stirred at room temperature for 1 hour. The solvent was evaporated under reduced pressure, and 2-aminoethanol (20 mL) was added thereto, followed by stirring at 70 C. for 2 hours. After cooling, the reaction mixture was purified by silica gel column chromatography (chloroform:methanol=30:1 to 20:1) to give Compound Aa (28 g, 60%) as a pale yellow oily substance. [0449] 1H NMR (270 MHz, CDCl3) δ7.00-6.78 (1H, m), 6.30-6.12 (1H, m), 4.19 (2H, q), 3.91-3.60 (4H, m), 3.57-3.30 (2H, m), 2.80-2.55 (3H, m), 1.29 (3H, t).
With potassium carbonate; In tetrahydrofuran; at 100℃;
Ethyl 3-(3-fluoro-2-nitrophenylamino)propionate (Step 1). A round bottomed flask was charged with ethyl 3-aminopropanoate hydrochloride (1 g, 6.51 mmol), l,3-difluoro-2- nitrobenzene (1.036 g, 6.51 mmol), potassium carbonate (2.70 g, 19.53 mmol), and a stirbar. THF (35 mL, 0.2 M) was added, and the mixture was stirred at 100 C overnight. The mixture was concentrated with celite and purified by silica gel chromatography (eluting withhexanes/ethyl acetate) to yield ethyl 3-(3-fluoro-2-nitrophenylamino)propionate as a yellow amorphous solid (1.473g, 5.75 mmol, 88%).
With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20 - 80℃; for 4h;
Example 79: Ethyl 3-((4-bromothiazol-2-yl)methylamino)propanoate [00229] A mixture of <strong>[167366-05-4]4-bromothiazole-2-carbaldehyde</strong> (1.91 g, 10.0 mmol, 1.0 eq), ethyl 3-aminopropanoate HC1 (1.75 g, 15.0 mmol, 1.5 eq) in DCE (30 mL) was stirred at 80C for 2 h. The mixture was cooled down to rt, and NaBH(AcO)3 (5.3 g, 25.0 mmol, 2.5 eq) was added, the resultant mixture was stirred at rt for 2 h. The reaction mixture was diluted with EA (60 mL), followed by filtration, the filtrate was concerntrated in vacuo, and the residue was purified by column chromatography on silica gel (PE/EA = 5/1) to give the title compound as a yellow oil (1.1 g, 37% yield). LCMS mlz 293.0 [M+H].
With triethylamine; In dichloromethane; at 0 - 20℃; for 4h;
Example 174 [0591] ethyl 3-aminopropanoate, HCl salt (300 mg, 1.95 mmol) in dichloromethane (25.0 mL) and triethylamine (0.817 mL, 5.86 mmol) was treated at 0 C. with <strong>[42926-52-3]2-ethoxybenzoyl chloride</strong> (361 mg, 1.95 mmol). The reaction mixture was stirred at 0 C. for 2 h and at room temperature for 2 h. The reaction mixture was concentrated and purified via silica gel chromatography using a gradient of 0-100% of EtOAc in hexanes to give 478 mg (92%) of the title product as a colorless oil which was used directly in the next reaction without further purification. LC-MS Retention Time: t2 (Method 2)=3.346 min; m/z (M+H)+ 266.1.
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