Glycolic Acid → HCID 57550365, Verbindung

To a screw-cap vial was added glycolic acid (100 mg, 1.31 mmol), 1-(3-dimthylaminopropyl)-3-ethylcarbodiimide hydrochloride (277.3 mg, 1.45 mmol), hydroxybenzotriazole (195.5 mg, 1.45 mmol), 1-(2,4-dichlorophenyl)-piperazine dihydrochloride (439.8 mg, 1.45 mmol), triethylamine (0.55 mL, 3.94 mmol) and N,N-dimethylformamide (5 mL). The resulting mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate (8 mL), successively washed with water (8 mL), saturated aqueous sodium bicarbonate (2×8 mL) and water (8 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified on silica gel using hexanes:ethyl acetate=4:1 to 100% ethyl acetate in a gradient fashion, to isolate the desired product as yellow solid (171.1 mg, 45%). 1H NMR (300 MHz, CDCl3): δ 7.28 (d, 1H), 7.11 (dd, 1H), 6.85 (dd, 1H), 4.11 (br, 2H), 3.74 (t, 2H), 3.72 (br, 1H, OH), 3.36 (t, 2H), 2.92 (t, 4H)

1. washsuccessively washed with water (8 mL), saturated aqueous sodium bicarbonate (2×8 mL) and water (8 mL)
2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
3. filtrationfiltered
4. concentrationconcentrated in vacuo
5. customThe crude residue was purified on silica gel

ORD-Eintrag

ord-7b2ec6fd73b649a7b53cde26f00c03aa

Quelldatensatz

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07935703B2