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

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 (10percent 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.(MM-2-84) H-Nva (5-Ph) -OH (500 mg, 2.59 mmol) was suspended in anhydrous dioxane (5 mL) in a sealed tube reaction vessel. Cone. H2SO4 (200 muiota) was added, and the mixture was cooled to -78 C. Condensed isobutylene (approx. 4 mL) was transferred via cannula onto the frozen reaction mixture. The reaction vessel was sealed tightly and warmed to room temperature overnight (about 18 hours) . After stirring 2 days, pressure was slowly released, the mixture was diluted with Et20 (50 mL) and washed with sat. NaHC03 (25 mL) . The aqueous phase was extracted with Et20 (2 x 25 mL) , and the combined ethereal phases were dried over Na2S04 and concentrated thoroughly. H-Nva ( 5-Ph) -OtBu (464 mg, 72%) obtained as a yellow oil was used without further purification. 1H NMR (500 MHz, CDC13) delta 7.30 - 7.25 (m, 2H) , 7.21 - 7.16 (m, 3H) , 3.37 - 3.28 (m, 1H) , 2.65 (m, 2H) , 1.71 (m, 4H) , 1.45 (s, 9H) .Example 23: (S)-2-(5-methoxybenzofuran-2-carboxamido)-5-phenylpentanoic acidTo (S)-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 (23 mg, 0.12 mmol) was dissolved in H2O (1 mL) containing equimolar amounts of NaOH (5 mg, 0.12 mmol). The solution was cooled to 0 C., then m-Toluic acid chloride (16 muL, 0.12 mmol) was added dropwise under vigorous stirring. The mixture was allowed to warm to room temperature and stirred for approx. 12 h. After acidification with 1 M HCl (1 mL), the product was extracted from the reaction mixture with DCM (4 mL). The organic layer was separated and the solvent was removed in vacuo to yield (S)-2-(3-methyl-benzoylamino)-5-phenyl-pentanoic acid 3 (21 mg, 56%) as a white solid: 1H-NMR (400 MHz, CD3OD) delta=7.83-7.09 (m, 9H), 4.62 (dd, J=5.0, J=9.1, 1H), 2.65 (m, 2H), 2.37 (s, 3H), 2.01-1.67 (m, 4H). MS calcd. for C19H22NO3 (M+H+) 312.16, found 312.4.

Molecular Weight:193.24
XLogP3:-0.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:5
Exact Mass:193.110278721
Monoisotopic Mass:193.110278721
Topological Polar Surface Area:63.3
Heavy Atom Count:14
Complexity:176
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes