These common heterocyclic compound, 1546-79-8, name is 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone, its 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. COA of Formula: C5H3F3N2O
General procedure: The compound 6b (35.1 mg, 50 mumol) was dried by repeated coevaporations with dry MeCN (3 mL) under Ar. The thymidine 3?-O-oxazaphospholidine derivative 7t (75.5 mg, 0.10 mmol), which was dried in vacuo overnight, and a 0.3 M solution of CMPT 8 (0.5 mL), which was dried over MS3A overnight, were successively added, and the mixture was stirred for 20 min at rt under Ar. N-(Trifluoroacetyl)imidazole (17.0 muL, 0.15 mmol) and i-Pr2NEt (44.0 muL, 0.25 mmol) were added and the mixture was stirred for 30 min at rt. Then DTD (31.9 mg, 0.15 mmol) was added and the mixture was stirred for 50 min at rt. The mixture was then concentrated under reduced pressure, and the residue was dissolved in dichloromethane (5.0 mL). A 6 vol% DCA solution in dichloromethane (5.0 mL) and Et3SiH (1.2 mL, 7.5 mmol) were added and the mixture was stirred for 20 min at rt. The mixture was washed with saturated NaHCO3 aqueous solutions (3 ¡Á 10 mL). The aqueous layers were combined and back-extracted with dichloromethane (2 ¡Á 10 mL). The organic layers were combined, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by FSPE [1.6 cm column id, 4.8 g of fluorous silica gel, methanol-H2O 16 mL (80:20, v/v) then THF 25 mL] to give 14t, a, c or g as a colorless foam, which was analyzed by 31P NMR (Fig. 2). The 14t, a, c or g thus obtained was dissolved in ethanol (8.0 mL) and a 25% NH3 aqueous solution (40 mL) was added. The mixture was put in a sealed flask and heated at 55 C for 12 h while stirring. The mixture was then cooled to rt, concentrated under reduced pressure to ca. 20 mL The mixture was diluted with a 0.1 M ammonium acetate buffer (pH 7.0) (20 mL) and washed with CHCl3 (4 ¡Á 20 mL). The aqueous layer was then concentrated under reduced pressure. The residue was repeatedly lyophilized from distilled H2O to remove ammonium acetate to give crude the dinucleoside phosphorothioate (15t, a, c or g), which was analyzed by RP-HPLC [Senshu Pak PEGASIL ODS, 4 ¡Á 150 mm, linear gradient of 0-20% MeCN (60 min) in 0.1 M triethylammonium acetate buffer (pH 7.0), 50 C, 0.5 mL/min]. Authentic samples of 15t,a,c,g were synthesized via the solid-phase synthesis using the nucleoside 3?-O-oxazaphospholidines 7t,a,c,g as monomer units [8d].
The synthetic route of 2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone has been constantly updated, and we look forward to future research findings.
Reference:
Article; Oka, Natsuhisa; Murakami, Ryosuke; Kondo, Tomoaki; Wada, Takeshi; Journal of Fluorine Chemistry; vol. 150; (2013); p. 85 – 91;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem