Hydrochloric Acid → 2-(4-Adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid

To a solution of 2-(4-adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid methyl ester (100 mg, 0.24 mmol) in dimethyl sulfide (5 ml) and dichloromethane (5 ml) was added aluminum bromide (1.02 g, 3.84 mmol). The reaction mixture was stirred at room temperature for 2.5 h, after which water and 10% HCl were added. After stirring at room temperature for 1 h, the mixture was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried (MgSO4 anh), and concentrated. The residue was purified by silica gel flash column chromatography (CH2Cl2:MeOH=4:1) to give 2-(4-adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid as a white solid (63.8 mg, 66.0% yield).

1. stirringAfter stirring at room temperature for 1 h
2. customthe mixture was partitioned between ethyl acetate and water
3. washThe organic phase was washed with brine
4. dry with materialdried (MgSO4 anh)
5. concentrationconcentrated
6. customThe residue was purified by silica gel flash column chromatography (CH2Cl2:MeOH=4:1)

ORD-Eintrag

ord-b38082bd0ab241e3971552f101bbf1f3

Quelldatensatz

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08394799B2