ChemicalBook CAS DataBase List L-2-AMINO-5-PHENYL-PENTANOIC ACID

L-2-AMINO-5-PHENYL-PENTANOIC ACID synthesis

8synthesis methods

Product Name:L-2-AMINO-5-PHENYL-PENTANOIC ACID
CAS Number:62777-25-7
Molecular formula:C11H15NO2
Molecular Weight:193.24

4-Pentenoic acid, 2-amino-5-phenyl-, (2S,4E)-

52161-76-9

62777-25-7

L-styrylalanine (CAS: 52161-76-9, 50 mg, 0.26 mmol) was used as starting material, which was dissolved in methanol (5 mL) and the reaction vessel was flushed with nitrogen. Subsequently, a catalytic amount of 10% palladium/carbon catalyst was added. The reaction vessel was placed under hydrogen atmosphere and the reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, the catalyst was filtered through diatomaceous earth to remove the catalyst. The filtrate was concentrated under reduced pressure to remove the organic solvent to afford the target product (S)-2-amino-5-phenylpentanoic acid (51 mg, quantitative yield) as a white powder. The structure of the product was confirmed by 1H-NMR (400 MHz, CD3OD): δ= 7.42-7.25 (m, 5H), 3.71 (t, J = 6.0 Hz, 1H), 2.69 (t, J = 6.4 Hz, 2H), 1.85 (m, 2H), 1.70 (m, 2H). Mass spectrometry result: C11H16NO2 ([M+H]+) calculated value 194.12, measured value 194.4.

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Yield:62777-25-7 100%

Reaction Conditions:

with hydrogen;palladium 10% on activated carbon in methanol at 20; for 2 h;

Steps:

2.A Preparation 2. (S)-N-{1-[2-(4-Methoxy-phenylamino)-ethylcarbamoyl]-4-phenyl-butyl}-3-methyl-benzamide; Step A

L-Styryl alanine 1 (50 mg, 0.26 mmol) was dissolved in MeOH (5 mL) and the reaction vessel was flushed with nitrogen. Catalytic amount of palladium (10% on carbon) was added and the reaction vessel was placed under a hydrogen atmosphere. The mixture was stirred for 2 h at room temperature, then filtered over celite. The organic solvent was removed in vacuo to yield (S)-2-amino-5-phenyl-pentanoic acid 2 (51 mg, quant.) as a white powder: 1H-NMR (400 MHz, CD3OD) δ=7.42-7.25 (m, 5H), 3.71 (t, J=6.0, 1H), 2.69 (t, J=6.4, 2H), 1.85 (m, 2H), 1.70 (m, 2H). MS calcd. for C11H16NO2 (M+H+) 194.12, found 194.4.

References:

US2004/198780,2004,A1 Location in patent:Page 23

88768-11-0 Synthesis