Tetrahydrofuran → Benzamide

After cooling N,N-dimethyl-1-phenylethane-1,2-diamine represented by Formula 101 (292 mg, 1.78 mmol, purchased from Alfa Aesar Co.) and triethylamine (0.55 mL, 3.95 mmol) in THF (8 mL) at 0° C. under a nitrogen atmosphere, 4-n-benzyloxy-3,5-dimethoxybenzoic acid chloride represented by Formula 85 (606 mg, 1.98 mmol) prepared in Preparative Example 1 in THF (12 mL) was slowly added to the cooled solution. After agitating the above solution at the same temperature for 30 minutes, this was left alone at room temperature for 18 hours. A precipitate generated during the reaction was filtered and discarded, the remaining solution was diluted using chloroform and washed with a potassium carbonate solution, followed by separation and drying with sodium sulfate. The solvent was removed again under reduced pressure. The obtained vacuum-concentrated mixture was subjected to separation and purification through column chromatography (ethyl acetate/hexane/triethylamine, 2:1:0.1, v/v/v) using silica gel (SiO2), resulting in a benzamide compound represented by Formula 19 as a desired product (VVZ-020; 451.3 mg, 52% yield).

1. additionwas slowly added to the cooled solution
2. waitthis was left alone at room temperature for 18 hours
3. filtrationwas filtered
4. additionthe remaining solution was diluted
5. washwashed with a potassium carbonate solution
6. customfollowed by separation
7. dry with materialdrying with sodium sulfate
8. customThe solvent was removed again under reduced pressure
9. concentrationThe obtained vacuum-concentrated mixture
10. customwas subjected to separation and purification through column chromatography (ethyl acetate/hexane/triethylamine, 2:1:0.1, v/v/v)

ORD record

ord-b0965d781a834d60a1e93eb3292e3e48

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09359346B2