Application of 60792-79-2, The chemical industry reduces the impact on the environment during synthesis 60792-79-2, name is 2,2′-Oxybis(ethylamine) dihydrochloride, I believe this compound will play a more active role in future production and life.
Example 6; Preparation of (4Z,7Z,10Z,13Z,16Z,19Z)-N-(2-(2-((E)-6-(4-hydroxy-6-methoxy-7- methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methylhex-4- enamido)ethoxy)ethyl)docosa-4,7,10,13,16,19-hexaenamide (I-2); In a typical run, sodium hydroxide (400 mg, 10 mmol) was dissolved in MeOH (70 mL) and 2-(2-aminoethoxy)ethanamine dihydrochloride (1.0 g, 5.65 mmol) was added. The resulting reaction mixture was stirred at room temperature for 30 min A solution containing Boc2O (740 mg, 3.40 mmol) in THF (15 mL) was then added dropwise, at room temperature, over a period of 15 min The resulting reaction mixture was stirred at room temperature for 18 h, and then concentrated under reduced pressure. The resulting residue was taken up in CH2Cl2 (200 mL) and stirred vigorously at room temperature for 4 h. The mixture was filtered and the filtrate was concentrated under reduced pressure to afford tert-butyl 2-(2-aminoethoxy)ethylcarbamate (850 mg, 74%).tert-Butyl 2-(2-aminoethoxy)ethylcarbamate (1.47 mmol) was then taken up in CH3CN (10 mL) along with mycophenolic acid (470 mg, 1.47 mmol) and EDCI (310 mg, 1.62 mmol). The resulting reaction mixture was stirred at room temperature for 18 h. It is then diluted with EtOAc (50 mL), washed with saturated aqueous NaHCO3, brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (9:1 CH2Cl2/MeOH) to afford 620 mg of (E)-tert-butyl 2-(2-(6- (4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methylhex-4- enamido)ethoxy)ethylcarbamate (83% yield).(E)-tert-Butyl 2-(2-(6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3- dihydroisobenzofuran-5-yl)-4-methylhex-4-enamido)ethoxy)ethylcarbamate (620 mg, 1.22 mmol) was taken up in 10 mL of 4 M HC1 in dioxane and allowed to stir at room temperature for 2 h. The resulting reaction mixture was concentrated under reduced pressure to afford the HCl salt of (E)-N-(2-(2-aminoethoxy)ethyl)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3- dihydroisobenzofuran-5-yl)-4-methylhex-4-enamide This material was taken up in CH3CN (10 mL) along with (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid (400 mg, 1.22 mmol), HATU (510 mg, 1.34 mmol) and DIEA (640 muL, 3.66 mmol). The resulting reaction mixture was stirred at room temperature for 2 h. It was then diluted with EtOAc and washed successively with saturated aqueous NaHCO3 and brine. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by silica gel chromatography (5% MeOH in CH2Cl2) afforded 600 mg of (4Z,7Z,10Z,13Z,16Z,19Z)-N-(2- (2-((E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4- methylhex-4-enamido)ethoxy)ethyl)docosa-4,7,10,13,16,19-hexaenamide (68% yield). MS (EI) calcd for C43H60N2O7: 716.44; found 717 (M+1).
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2,2′-Oxybis(ethylamine) dihydrochloride, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; CATABASIS PHARMACEUTICALS, INC.; US2011/213028; (2011); A1;,
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