β-Phenyl-L-phenylalanine

White powder

Step 2: After 1, 1-dimethylethyl-(2R)-(2, 6-dichlorophenyl)-(4S)-(diphenylmethyl)-5-oxo-3-((1'R)-phenylethyl)tetrahydro-1H -1-imidazolecarboxylate (188 mg, 0.31 mmol) was dissolved in a mixed solvent of 7.5 ml of tetrahydrofuran and 1 ml of a 1M hydrochloric acid, the atmosphere of the reaction vessel was replaced with nitrogen. To the mixture was added 90 mg of 20percent palladium hydroxide-carbon; and the atmosphere was replaced with nitrogen gas again, and then the atmosphere was replaced with hydrogen gas. After reaction was carried out at room temperature under 2.2 MPa of hydrogen pressure for 100 hours, the catalyst was separated by filtration. The resulting product was washed with 5 ml of tetrahydrofuran three time and 1 ml of distilled water once respectively, and the solvent was removed in reduced pressure. To the mixture was added 7.5 ml of a 6 M hydrochloric acid; and the mixture was heated and refluxed at an outer temperature of 120 to 130°C for 2.5 hours. Thereafter, the reaction mixture was cooled to an outer temperature of 0°C. After the pH was adjusted to 6 to 7 by adding a 30percent aqueous solution of sodium hydroxide thereto, the solvent was removed in reduced pressure. The quantity of (2S)-2-amino-3, 3-diphenylpropionic acid contained in the residue was determined in the following analysis condition; and as a result, the yield was 76percent at 95.7percent ee.To a solution of Step E. Preparation (25)-2-methoxycarbonylamino-3, 3-diphenyl-propionic acidTo a solution of To a solution of 6-(Fmoc-amino)hexanoic acid (4, 50 mg, 0.14 mmol), EDC(35 mg, 0.18 mmol) and DMAP (2 mg, 0.015 mmol) were dissolved in DCM anhydrous (4 mL). The temperature was brought to 0 Cand NHS (21 mg, 0.18 mmol) was added. The solution was allowed to reach room temperature and it was left stirring for 6 h. Water was subsequently mixed to the solution. The aqueous layer was extracted with DCM (4 10 mL), the organic layers were combined, washed with brine, dried over NaSO4 and concentrated invacuo to afford the product as a white powder. The crude product was dissolved in DMF anhydrous (10 mL) with 3, 3-Diphenyl-L-alanine (1, 50.0 mg, 0.21 mmol) was dissolved in DMF anhydrous (8 mL) and FITC (2, 160.0 mg, 0.41 mmol) was added together with DIPEA (358 muL, 2.07 mmol). The solution was left stirring in darkness overnight. The solvent was removed in vacuo, the crude product was redissolved in EtOAc and acetic acid 5% was mixed. The aqueous layer was extracted with EtOAc (3 Chi 20 mL), the organic layers were combined, washed with brine, dried over NaSO4 and concentrated in vacuo. The crude product was purified via prep HPLC from 30% to 100% of phase B over 45 min to achieve 3 as a yellow solid (102 mg, 77% yield). Retention time analytical HPLC from 30% to 100% of phase B over 30 min: 14.183 min. NMR, delta (500 MHz, DMSO), 10.10 (2H, s, OH FITC), 8.26 (1H, s, CH FITC), 8.07 (1H, d, J = 8.4 Hz, NHCO Bip), 7.54 (1H, d, J = 8.3 Hz, CH FITC), 7.39-7.18 (10H, m, Ph Bip), 7.09 (1H, d, J = 8.3 Hz, CH FITC), 6.66 (2H, s, 2CH FITC), 6.59-6.53 (4H, m, CH FITC), 5.78 (1H, t, J = 9.2 Hz, CHNH Bip), 4.54 (1H, d, J = 9.9 Hz, CHPh2 Bip). 13C NMR delta (126 MHz, DMSO) 180.51 (CS FITC), 172.08, 168.33, 159.45, 151.84 and 147.27 (FITC), 140.91, 140.81, 140.68, 129.15, 129.04, 128.46, 128.36, 128.33, 128.22, 126.77 and 126.70 (Ph Bip and FITC), 126.50, 124.05, 116.22, 112.52, 109.61 and 102.16 (FITC), 59.75 (CHNH Bip), 52.78 (CHPh2 Bip). ESI-MS m/z, M+H+ = 631.1, calculated for C36H26N2O7S = 630.2.

Molecular Weight:241.28
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:241.110278721
Monoisotopic Mass:241.110278721
Topological Polar Surface Area:63.3
Heavy Atom Count:18
Complexity:250
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes