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ChemicalBook CAS DataBase List (S)-2-Amino-3-(4-(trifluoromethoxy)phenyl)propanoic acid hydrochloride
921609-34-9

(S)-2-Amino-3-(4-(trifluoromethoxy)phenyl)propanoic acid hydrochloride synthesis

3synthesis methods
L-Tyrosine, N-acetyl-O-(trifluoromethyl)-, methyl ester

921623-42-9

(S)-2-Amino-3-(4-(trifluoromethoxy)phenyl)propanoic acid hydrochloride

921609-34-9

General procedure for the synthesis of (S)-2-amino-3-(4-(trifluoromethoxy)phenyl)propanoic acid hydrochloride from the compound (CAS: 921623-42-9): methyl (2S)-2-(acetylamino)-3-[4-(trifluoromethoxy)phenyl]propanoate (29.9 mg, 0.098 mmol) prepared in Reference Example 3 was mixed with 6 N hydrochloric acid ( 330 μL) were mixed and the reaction was stirred at 100 °C for 4 hours. Upon completion of the reaction, the reaction solution was cooled to room temperature and subsequently concentrated under reduced pressure. The resulting residue was azeotroped with toluene, washed with ether and dried under reduced pressure to give 26 mg (S)-2-amino-3-(4-(trifluoromethoxy)phenyl)propionic acid hydrochloride (white powder, yield: 93%).

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Yield:921609-34-9 93%

Reaction Conditions:

with hydrogenchloride;water at 100; for 4 h;Product distribution / selectivity;

Steps:

3g (3g) (2S)-2-Amino-3-[4-(trifluoromethoxy)phenyl]propanoic acid hydrochloride

(3g) (2S)-2-Amino-3-[4-(trifluoromethoxy)phenyl]propanoic acid hydrochloride A 6 N hydrochloric acid (330 μL) solution of methyl (2S)-2-(acetylamino)-3-[4-(trifluoromethoxy)phenyl]propanoate (29.9 mg, 0.098 mmol) prepared in Reference Example 3 (3f) was stirred at 100°C for 4 hours. The reaction solution was cooled to room temperature and then concentrated under reduced pressure. The obtained residue was azeotroped with toluene, washed with diethyl ether, and dried under reduced pressure to give 26 mg of the title compound (white powder, yield: 93%).

References:

EP1908466,2008,A1 Location in patent:Page/Page column 121