Cbz-3-(2-Naphthyl)-D-alanine

White to off-white powder

To DMF solution (100 ml) of CBZ-D-3-(2-naphthyl)alanine 9.0 g (25.8 mmol) under cooling on ice-water, HOBt 3.8 g (28 mmol), EDC 5.4 g (28 mmol) were added, stirring was continued for 30 min. N-(3-Amino-2-hydroxypropyl)phthalimide-hydrochloride 6 g (23.4 mmol), NMM 2.8 g (28 mmol) were added to the reaction mixture and then stirred at room temperature overnigth. The reaction mixture was poured into saturated sodium bicarbonate solution (400 ml) and formed precipitate was collected by filtration, washed with water. Purification by silica gel chromatography gave a desired product (11.3 g). NMR, FAB-MS spectra were consistent with the desired title product. 1H-NMR(270 MHz, CDCl3)delta: 3.00-3.55(6H, m), 3.79(1H, bd, J=19.1 Hz, ), 4.55(1H, dd, J=7.3 Hz), 5.04(2H, s), 5.50-5.60(1H, m), 6.65-6.80(1H, m), 7.20-7.45(8H, m), 7.65-7.85(8H, m). FAB-MS: m/z 552(M+H)+Step 1 [3-(2(R)-Amino-3-naphthalen-2-yl-propionylamino)propyl]carbamic acid, tert-butyl ester To DMF(15 ml) solution of CBZ-D-Nal-OH(1.1 g) and N-(3-Aminopropyl) carbamic acid tert-butyl ester (500 mg), HOBt(530 mg), EDC(720 mg) were added under cooling on ice-water and then stirring was continued at room temperature overnight. The reaction mixture was poured into saturated sodium hydrogen carbonate solution (150 ml), formed precipitate was collected by filtration and then dried to give white powder (1.43 g). Obtained white powder (1.43 g) in DMF (15 ml) is hydrogenated with 10% Pd-C(400 mg) at 35 C., 4.3 atm. for 4 days. After removal of catalyst by filtration, filtrate was evaporated to dryness and then crystallized from n-hexane:ethyl acetate. The crystal was collected and then dried to afford 640 mg of product. 1HMR (270 MHz, CDCl3)delta: 1.34(2H, s), 1.43(9H, s), 1.59(2H, m), 2.90(1H, dd), 3.05(2H, q), 3.32(2H, q), 3.41(1H, dd), 3.70(1H, bs), 5.02(1H, bs), 7.38(1H, d), 4.40-7.55(3H, m), 7.66(1H, s), 7.75-7.85(3H, m) FAB-MSS: m/z 370(M+H)+

Molecular Weight:349.4
XLogP3:4.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:7
Exact Mass:349.13140809
Monoisotopic Mass:349.13140809
Topological Polar Surface Area:75.6
Heavy Atom Count:26
Complexity:475
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes