Hydrochloric Acid → 2-(Phenylamino)propanoic acid

Temperatur

100 °C

A mixture of alanine (356 mg, 4.0 mmol), iodobenzene (816 mg, 4.0 mmol), trans-dichlorobis(tri-o-tolylphosphine)palladium(II) {Pd[P(o-Tol)3]2Cl2} (160 mg, 0.2 mmol), copper(I) iodide (40 mg, 0.2 mmol), K2CO3 (552 mg, 4.0 mmol), benzyltriethylammonium chloride (160 mg, 0.8 mmol), triethylamine (1.6 mL) and water (0.8 mL) in DMF (8 mL) was stirred under nitrogen atmosphere at 100° C. for 20 hours. The mixture was cooled to room temperature, diluted with ethyl acetate (50 mL) and water (50 mL), acidified with 6N HCl to the pH=2 to 3. The aqueous layer was extracted with ethyl acetate (50 mL×4). The combined organic layers were washed with water, brine, dried over anhydrous Na2SO4, filtered and evaporated in vacuo to give a red oil. Flash chromatography using hexane/ethyl acetate/acetic acid (95/5/0.5 to 80/20/0.5) to afford 300 mg (45% yield) of the title compound as a pink solid. 1H-NMR (500 MHz, CDCl3/CD3OD=0.5 ml/3 drops) δ 1.45 (d, 3H), 4.02-4.15 (m, H), 6.57-6.70 (m, 3H), 7.11-7.25 (m, 2H); Analytical HPLC: 6.10 min. LC-MS: m/e=166 (M+H+).

1. temperatureThe mixture was cooled to room temperature
2. extractionThe aqueous layer was extracted with ethyl acetate (50 mL×4)
3. washThe combined organic layers were washed with water, brine
4. dry with materialdried over anhydrous Na2SO4
5. filtrationfiltered
6. customevaporated in vacuo
7. customto give a red oil

ORD-Eintrag

ord-f521e4f4c0254f28b604189a0262906d

Quelldatensatz

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07358273B2