p-Nitrophenylalanine

white to light yellow crystal powde

Preparation Procedures: To the solution of l-phenylalanine (8) (8.26 g, 50.0 mmol) in HA mixture of 44 mL of conc. HNO3 and 34.6 mL of conc. H2SO4 was added dropwise to a solution of 50 g (0.303 mol) of L(D)-phenylalanine in 150 mL of 85percent H2SO4, pre-cooled to 10°C. The reaction mixture was stirred for 3 hours at 8–10°C, then the reaction mixture was adjusted to pH 6 by addition of NaOH aqueous solution. The precipitate was filtered off and dried. The reaction product was recrystallized from water. Yield 91percent (2), 89percent (2b). mp 240°C (mp 239–241°C [10]). IR spectrum ν, cm–1: 3294, 2889, 1701, 1620, 1535, 1443, 1350, 880, 864, 745, 698, 525. 1 NMR spectrum (DMSO-d6), δ, ppm: 2.90–4.00 m (5H, CH, CH2, NH2), 7.55 d (2Harom, 3J 8.5 Hz), 8.15 d (2Harom, 3J 8.5 Hz). 13 NMR spectrum (DMSO-d6), δ, ppm: 40.79 (2), 57.28 (), 128.15, 129.79, 145.41, 168.48 (arom), 172.84 (). Mass spectrum (ESI), m/z: 211.0713 [M + H]+. C9H10N2O4. Calculated M210.0641.A mixed solution of concentrated HNOTo a solution of Np, a mixture of 3 mL concentrated nitric acid, 3.75 mL concentrated sulfuric acid and 2.75 g Lphenylalanine(17 mmol) was put in a 100mL round bottom flask while heating an ice bath for 1 h. The reaction mixture was stirred for another 2 h at 25oil bath. The yellow crystallizations were appeared when adding ammonia. Afterdried, filtered and evaporated, 3.1g yellow powder was obtained and the yield was 87percent (Fig. 1E)In a round bottom flask, conc. H(1) 55 mmol of phenylalanine was dissolved with 25.0 mL of 85percent H2SO4, added dropwise to 12.5 mL of HNO3-H2SO4 mixed acid (V/V=1.4/1.1), reacted at room temperature for 1 h, and thereafter pH was adjusted to 6 with aqueous ammonia, and the precipitate was collected to obtain about 9 g of 2-amino-3-(4-nitrophenyl) propanoic acid (2-amino-3-(4-nitrophenyl) propanoic acid).General procedure: Kinetic resolution of (RS)-2-acetamido-2-phenylacetic acid (Table 2, entry 1). A 25 ml round-bottomed flask was charged with (RS)-2-acetamido-2-phenylacetic acid at a concentration of 50 mM and 5 mL of phosphorus buffer solution at pH 6.5. Next, 4.2 mg of free enzyme powder of lipase AS ‘Amano’ was added to the mixture. When this was completed, the resulting mixture was stirred at 35 °C for 24 h. Yields and ee values of the products were determined by HPLC analysis. When the reaction was completed, the solution was filtered through a pad of cotton. The solution was changed to pH 7.0, extracted with ethyl acetate three times, and the combined organic solution was dried over anhydrous magnesium sulfate and then evacuated to remove the organic solvent. The resulting residues were purified by column chromatography on silica gel with petroleum ether/ethyl acetate (1:10–1:5) to afford the pure amino acids.

Molecular Weight:210.19
XLogP3:-1.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:3
Exact Mass:210.06405680
Monoisotopic Mass:210.06405680
Topological Polar Surface Area:109
Heavy Atom Count:15
Complexity:243
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes