2-Fluoro-L-phenylalanine → HCID 28804565, compound

To a solution of (2S)-2-amino-3-(2-fluorophenyl)propanoic acid (10.00 g, 54.59 mmol) in tetrahydrofuran (25 mL) with stirring was added 1.0 M borane-THF complex in THF (100.0 mL) (freshly opened) dropwise to keep the internal temperature around 0° C. After addition, the reaction mixture was stirred at room temperature for 3 hrs. Then the mixture was cooled with an ice-bath, quenched with AcOH:MeOH (1:5, 50 mL), and partitioned between saturated aqueous NaHCO3 solution and dichloromethane (DCM). The organic phases were dried over sodium sulfate, filtered, and evaporated under vacuum to give an oil residue which was purified on prep. HPLC to give the purified desired product. LC-MS found: 170.1 (M+H)+.

1. customthe internal temperature around 0° C
2. additionAfter addition
3. temperatureThen the mixture was cooled with an ice-bath
4. customquenched with AcOH:MeOH (1:5, 50 mL)
5. custompartitioned between saturated aqueous NaHCO3 solution and dichloromethane (DCM)
6. dry with materialThe organic phases were dried over sodium sulfate
7. filtrationfiltered
8. customevaporated under vacuum
9. customto give an oil residue which
10. customwas purified on prep
11. customHPLC to give the
12. custompurified desired product

ORD record

ord-433eeab4adf940008d101c38e9f6de87

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08895571B2