Trifluoroacetic acid → HCID 21098500, compound

The compound prepared in Example 181 (700 mg) was dissolved in chloroform (3 ml), and 95% trifluoroacetic acid (3 ml) was added dropwise to the solution at room temperature. The reaction mixture was stirred at room temperature for 2 hr and was then concentrated. Potassium carbonate (690 mg) and dimethylformamide (3 ml) were added to the concentrate, and the mixture was stirred. A solution (2 ml) of (1-bromoethyl)benzene (408 mg) in acetonitrile was added dropwise to the reaction mixture. The reaction mixture was stirred at room temperature for 18 hr. A saturated aqueous sodium hydrogencarbonate solution (3 ml) was then added thereto, and the mixture was extracted with chloroform-propanol (3/1). The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under the reduced pressure. The residue was purified by HPLC [chloroform/methanol] to give 185 mg of the title compound as two diastereomers (ratio=ca. 50:50).

1. concentrationwas then concentrated
2. additionPotassium carbonate (690 mg) and dimethylformamide (3 ml) were added to the concentrate
3. stirringthe mixture was stirred
4. additionA solution (2 ml) of (1-bromoethyl)benzene (408 mg) in acetonitrile was added dropwise to the reaction mixture
5. stirringThe reaction mixture was stirred at room temperature for 18 hr
6. additionA saturated aqueous sodium hydrogencarbonate solution (3 ml) was then added
7. extractionthe mixture was extracted with chloroform-propanol (3/1)
8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
9. customthe solvent was removed by distillation under the reduced pressure
10. customThe residue was purified by HPLC [chloroform/methanol]

ORD record

ord-60ceb635a32a4cd6ba5c9ac57c523b5b

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07217722B2