If you are hungry for even more, make sure to check my other article about 16681-70-2, the application of this compound in the production field has become more and more popular.
New discoveries in chemical research and development in 2021. The dynamic chemical diversity of the numerous elements, ions and molecules that constitute the basis of life provides wide challenges and opportunities for research. 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. Safety of 1H-[1,2,3]Triazole-4-carboxylic acid
Example 16 (R)-5-(5?-Chloro-2?-fluorobiphenyl-4-yl)-2-(2-hydroxyethyl)-2-hydroxymethyl-4-[(3H-[1,2,3]triazole-4-carbonyl)amino]pentanoic Acid (isomers a and b) [0438] 3-[(R)-2-Amino-3-(5?-chloro-2?-fluorobiphenyl-4-yl)-propyl]-3-hydroxymethyl-dihydro-furan-2-one (isomer a; 10 mg, 30 mumol, 1.0 eq.) and DIPEA (30 muL, 170 mumol, 5.6 eq.) were dissolved in DMF (200 muL). 1H-1,2,3-triazole-4-carboxylic acid (10 mg, 90 mumol, 3.0 eq.), DIPEA (60 muL, 340 mumol, 11.2 eq.) and HATU (15 mg, 40 mumol, 1.3 eq.), were dissolved in DMF (600 muL) and stirred at room temperature for a few minutes. The solutions were then combined and the resulting mixture stirred at room temperature and when the reaction was complete (as determined by LC/MS analysis), EtOAc and water were added to the mixture, the organics were then separated and concentrated in vacuo. The crude residue was dissolved in a 1:1 solution of MeOH and aqueous 2N NaOH (4 mL), and stirred at room temperature for 30 minutes and when the reaction was complete (as determined by LC/MS analysis), the mixture was concentrated in vacuo and purified by preparative HPLC to yield the title compound (isomer a; 3 mg). LCMS (ESI): calc. C23H24ClFN4O5=490; obs. M+H=491.2. Retention time: 2.04 min. [0440] 3-[(R)-2-Amino-3-(5?-chloro-2?-fluorobiphenyl-4-yl)-propyl]-3-hydroxymethyl-dihydro-furan-2-one (isomer b; 30 mg, 52 mumol, 1.0 eq.) and DIPEA (50 muL, 291 mumol, 5.6 eq.) were dissolved in DMF (200 muL). 1H-1,2,3-triazole-4-carboxylic acid (17 mg, 156 mumol, 3.0 eq.), DIPEA (100 muL, 582 mumol, 11.2 equiv.) and HATU (25 mg, 68 mumol, 1.3 eq.), were dissolved in DMF (600 muL) and stirred at room temperature for a few minutes. The solutions were then combined and the resulting mixture was stirred at room temperature; when the reaction was complete (as determined by LC/MS analysis), EtOAc and water were added to the mixture. The organic layer was separated, concentrated in vacuo and purified by preparative HPLC to yield the title compound (isomer b; 3.9 mg). LCMS (ESI): calc. C23H24ClFN4O5=490; obs. M+H=491.2. Retention time: 1.99 min. [0441] LC/MS Method: flow rate: 1.5 mL/min; Buffer A: 0.1% TFA/H2O; Buffer B 0.1% TFA/MeCN; gradient elution from 5-100% B over 3.6 minutes, then 100% B for 1.0 minute, detection at 254 nm
If you are hungry for even more, make sure to check my other article about 16681-70-2, the application of this compound in the production field has become more and more popular.
Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; Fleury, Melissa; Beausoliel, Anne-Marie; Hughes, Adam D.; Long, Daniel D.; Wilton, Donna A.A.; US2015/209352; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics