Methanol → HCID 10896843, Verbindung

Thionyl chloride (0.475 mL, 6.50 mmol) was added dropwise to a solution of (S)-4-fluorophenylglycine (commercially available from Sigma-Aldrich, Milwaukee, Wis.)(1.00 g, 5.91 mmol) in MeOH (25.0 mL), and the mixture was stirred at reflux for 2 hours. The reaction mixture was then concentrated to afford a brown oil. The residue was dissolved in EtOAc, and the solution was partitioned between EtOAc and saturated aqueous NaHCO3 solution. The aqueous phase was separated and extracted with EtOAc. The combined organic phases were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford (S)-methyl 2-amino-2-(4-fluorophenyl)acetate (1.1 g, 6.0 mmol, 100% yield) as a brown oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.28 (br. s., 2H), 3.59 (s, 3H), 4.55 (s, 1H), 7.05-7.23 (m, 2H), 7.31-7.53 (m, 2H). m/z (ESI) 184 (M+H)+.

1. temperatureat reflux for 2 hours
2. concentrationThe reaction mixture was then concentrated
3. customto afford a brown oil
4. customthe solution was partitioned between EtOAc and saturated aqueous NaHCO3 solution
5. customThe aqueous phase was separated
6. extractionextracted with EtOAc
7. washThe combined organic phases were washed with brine
8. dry with materialdried over anhydrous Na2SO4
9. filtrationfiltered
10. concentrationconcentrated

ORD-Eintrag

ord-ca7f0ffdd4074ea59384e6a982d2e5ca

Quelldatensatz

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09340549B2