Acrylic Acid → HCID 20786195, compound

To a solution of acrylic acid (2.50 g, 34.7 mmol) in dichloromethane (80 mL) at 0 degrees Celsius was added N-methyl-morpholine (4.73 g, 46.8 mmol), followed by isobutyl chloroformate (6.37 g, 46.8mmol). After 30 minutes, a solution of (2-amino-phenyl)-carbamic acid tertbutyl ester (5.80 g, 27.8 mmol) in dichloromethane (50 mL) was added dropwise to the refluxing reaction mixture over 30min. After the reaction was completed (2 hours later), the reaction mixture was allowed to cool down to room temperature, poured into ice water, and extracted with dichloromethane (30 mL×3). The organic layer was washed with water, dilute sodium bicarbonate solution, 0.1M HCl, water, and brine in turn. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude solid was recrystallized from ethyl acetate/petroleum ether=1/4 (v/v) to obtain the desired product (2.5g, 34%). MS: calc'd 263 (MH+), exp 263 (MH+).

1. custom2 hours
2. extractionextracted with dichloromethane (30 mL×3)
3. washThe organic layer was washed with water, dilute sodium bicarbonate solution, 0.1M HCl, water, and brine in turn
4. dry with materialThe organic layer was dried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe crude solid was recrystallized from ethyl acetate/petroleum ether=1/4 (v/v)

ORD record

ord-ddfae4d207fc42fe87aa896887f8a1a5

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07999000B2