Ammonium Chloride → HCID 86661753, compound

(2R)-(2-trifluoroacetamidopropyl)triphenylphosphonium iodide (8.3 g) synthesized according to J. Med. Chem. 2007, 50, 5627-5643 was dissolved in anhydrous tetrahydrofuran and cooled to −78° C. n-butyllithium (1.6 M n-hexane solution, 18.7 mL) was slowly added dropwise. After the dropwise addition, the mixture was stirred at room temperature for 20 minutes. Subsequently, the mixture was cooled to −78° C., and an anhydrous tetrahydrofuran (10 mL) solution of 2-benzyloxyacetaldehyde (2.35 g) was added. The mixture was gradually returned to room temperature and stirred at room temperature for 12 hours. After the completion of reaction, a saturated aqueous solution of ammonium chloride was added, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1) to obtain the compound of interest as a pale yellow oil (2.30 g, 52.6%).

1. additionwas slowly added dropwise
2. additionAfter the dropwise addition
3. temperatureSubsequently, the mixture was cooled to −78° C.
4. customwas gradually returned to room temperature
5. stirringstirred at room temperature for 12 hours
6. customAfter the completion of reaction
7. extractionfollowed by extraction with ethyl acetate
8. washThe organic layer was washed with saturated saline
9. dry with materialdried over anhydrous sodium sulfate
10. concentrationAfter concentration under reduced pressure
11. customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)

ORD record

ord-7610bff2e621472b871e697a021bf5a8

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08951997B2