ChemicalBook CAS DataBase List (2R)-2-AMINO-2-PHENYLBUTANOIC ACID

(2R)-2-AMINO-2-PHENYLBUTANOIC ACID synthesis

8synthesis methods

Product Name:(2R)-2-AMINO-2-PHENYLBUTANOIC ACID
CAS Number:33875-38-6
Molecular formula:C10H13NO2
Molecular Weight:179.22

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Yield:-

Reaction Conditions:

with water;sodium hydroxide at 130; for 48 h;Autoclave;

Steps:

14.1

In an autoclave, sodium hydroxide (17.120 g, 0.42803 mol) is solubilized in water (74 mL, 4.1 mol), then (5R)-5-ethyl-5-phenylimidazolidine-2,4-dione (20.0 g, 0.0979 mol) is added in portions. The reaction mixture is heated at 130° C. under stirring for 48 hours. The mixture is cooled down and a white precipitate forms.The pH is adjusted to 7 then the precipitate is washed with ethyl acetate. The mixture is diluted in 300 mL water cooled down to 0° C. The pH is adjusted to 1 with 12 M HCl (50.0 mL). The precipitate is completely dissolved. While maintaining the mixture at 0° C., the pH is adjusted to 7 with 20 mL of a 5N NaOH solution in order to obtain a white precipitate. The mixture is filtered, the precipitate is washed with water (150 mL) then dried under vacuum at 40° C. in order to produce 22.8 g of a white solid.NMR ¹H (MeOD): δ (ppm)=1.06 (3H, t, J=7.34 Hz, CH₃-CH₂), 2.30-2.38 (2H, m, CH₂-CH₃), 7.33-7.46 (3H, m, H_arom), 7.55-7.59 (2H, m, H_arom).

References:

US2009/197924,2009,A1 Location in patent:Page/Page column 12