Trifluoroacetic acid → 1-Benzyl-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid [2-(2,2,2-trifluoro-acetylamino)-ethyl]amide

{2-[(1-Benzyl-5-hydroxy-2-oxo-3-phenyl-1,2-dihydro-[1,7]naphthyridine-6-carbonyl)-amino]ethyl}-carbamic acid tert-butyl ester (25 mg, 0.049 mmol) was dissolved in CH2Cl2 (2 mL). Trifluoroacetic acid (1 mL) was added, and the mixture was stirred for 2 h. Solvent and excess TFA was removed by evaporation, and to the residue were added THF (3 mL), triethylamine (0.034 mL, 0.24 mmol), and ethyl trifluoroacetate (2 mL). The resulting mixture was refluxed overnight, then concentrated to dryness. The residue was dissolved in EtOAc and washed with 0.1 M HCl. The organic layer was dried over MgSO4 and concentrated, and the crude product was purified by silica gel chromatography (0-5% MeOH/CH2Cl2) to give 12.7 mg of the title compound as a light yellow solid. MS: (+) m/z 511.33 (M+1).

1. customSolvent and excess TFA was removed by evaporation
2. temperatureThe resulting mixture was refluxed overnight
3. concentrationconcentrated to dryness
4. dissolutionThe residue was dissolved in EtOAc
5. washwashed with 0.1 M HCl
6. dry with materialThe organic layer was dried over MgSO4
7. concentrationconcentrated
8. customthe crude product was purified by silica gel chromatography (0-5% MeOH/CH2Cl2)

ORDレコード

ord-2584487813a94760b5691d1839960fbd

出典データセット

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09271970B2