Ammonia → Ethyl acetate methanol ammonium hydroxide

Temperature

110 °C

A mixture of compound 27 (70 mg) and NH3 (7N in MeOH 4 mL, and 4 mL 28% aqueous) was heated under microwave at 110° C. for 2 hours. EtOAc (20 mL) and water (5 mL) were added to the reaction mixture. The organic layer was separated, concentrated and purified by column (EtOAc/MeOH 10/1, then EtOAc/MeOH/NH4OH 10/2/0.5) to afford a brown oil, which was dissolved in 0.5N HCl aqueous (20 mL), and freeze dried under vacuum to give compound 28 as a HCl-salt (brown solid, 40 mg, 58%): 1H-NMR (400 MHz, CD3OD) δ: 7.62-7.73 (m, 3H), 7.39-7.44 (m, 3H), 7.07-7.21 (m, 7H), 4.16-4.21 (m, 1H), 3.57-3.58 (m, 1H), 3.35-3.41 (m, 1H); LC/MS: m/z=372.1 [M+H]+ (Calc: 371.4).

1. customThe organic layer was separated
2. concentrationconcentrated
3. custompurified by column (EtOAc/MeOH 10/1

ORD record

ord-cff7fbde769f462e89caa3c541706e15

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09212139B2