3,5-Dihydroxybenzoic Acid → 3,5-Dihydroxybenzamide

After reaction step (a), the resulting amine (1 equiv.), 3,5-dihydroxybenzoic acid (1 equiv.), EDCI (1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride) (1.2 equiv.), HOBt (1-hydroxybenzotriazole hydrate) (1.2 equiv.), and Et3N (4 equiv.) in CH2Cl2.DMF (9:1) were stirred for 12 hours at room temperature. Then the reaction mixture was diluted with EtOAc and the organic layer washed with brine. The combined organic layer was dried over anhydrous Na2SO4 and concentrated. Purification of the resulting crude product by flash silica gel chromatography provided corresponding 3,5-dihydroxybenzamide derivative. The above derivative (1 equiv.) and active carbonate 4 (1.1 equiv.) in THF were stirred under hydrogen atmosphere in presence of Pd—C (10%) for 12 hours at room temperature. Then the reaction mixture was filtered and the organic layer washed with brine. The combined organic layer was dried over anhydrous Na2SO4 and concentrated. Purification of the resulting crude product by flash silica gel chromatography provided compound 134 as a solid.

1. customAfter reaction step (a)
2. washthe organic layer washed with brine
3. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
4. concentrationconcentrated
5. customPurification of the resulting crude product by flash silica gel chromatography

ORDレコード

ord-c781951f050045288ea58b6dbd9a58ca

出典データセット

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07157489B2