H-D-PHE-OTBUHCL

White powder

To a solution of N-[4-(heptylamino)phenyl]-4-methyl-benzenesulfonamide (44.0 mg, 0.122 mmol) obtained in step 49 1 in 6 dichloromethane (2.4 mL) were added 7 pyridine (29.7 mL, 0.366 mmol), 8 dimethylaminopyridine (1.50 mg, 0.0122 mmol) and 51 4-nitrophenyl chloroformate (34.2 g, 0.159 mmol) and the mixture was stirred for 2 hr. To the reaction mixture was added 31 D-phenylalanine t-butylester hydrochloride (62.9 mg, 0.244 mmol) and the mixture was stirred at room temperature overnight. To the reaction mixture was added 0.1N 10 hydrochloric acid (0.8 mL), and the mixture was extracted with dichloromethane. The solvent was evaporated and the obtained residue was purified by high performance liquid chromatography (water-acetonitrile (each containing 0.1percent 13 trifluoroacetic acid)) to give the 52 title compound (41.5 g, 0.0683 mmol, 56percent). MS (ESI) m/z 608 (M+H)+ (1948) 1H NMR (400 MHz, DMSO-d6) delta 8.74 (s, 1H), 7.38-7.33 (m, 2H), 7.33-7.28 (m, 2H), 7.28-7.20 (m, 4H), 7.20-7.13 (m, 3H), 6.83-6.75 (m, 2H), 6.35 (d, J=8.0 Hz, 1H), 4.38-4.28 (m, 1H), 2.97-2.85 (m, 2H), 2.32 (s, 3H), 1.28 (s, 9H), 1.25-1.04 (m, 12H), 0.76 (t, J=6.9 Hz, 3H).To a solution of N-(4-amino-2-fluoro-phenyl)-4-methyl-benzenesulfonamide (42.7 mg, 0.152 mmol) obtained in step 63 2 in 6 dichloromethane (1.5 mL) were added 16 triethylamine (0.106 mL, 0.762 mmol) and 17 carbonyldiimidazole (29.6 mg, 0.183 mmol) and the mixture was stirred for 1 hr. To the reaction mixture was added 31 D-phenylalanine t-butylester hydrochloride (86.4 mg, 0.335 mmol) and the mixture was stirred at room temperature overnight. To the reaction mixture was added 0.1N 10 hydrochloric acid (0.5 mL), and the mixture was extracted with dichloromethane. The solvent was evaporated and the obtained residue was purified by high performance liquid chromatography (water-acetonitrile (each containing 0.1percent 13 trifluoroacetic acid)) to give the 65 title compound (2.2 mg, 0.00417 mmol, 3percent). (1954) MS (ESI) m/z 528 (M+H)+ (1955) 1H NMR (400 MHz, DMSO-d6) delta 9.75 (s, 1H), 8.90 (s, 1H), 7.61-7.50 (m, 2H), 7.39-7.28 (m, 5H), 7.28-7.15 (m, 3H), 7.02 (t, J=8.8 Hz, 1H), 6.94-6.84 (m, 1H), 6.45 (d, J=7.9 Hz, 1H), 4.45-4.31 (m, 1H), 3.01-2.93 (m, 2H), 2.36 (s, 3H), 1.35 (s, 9H).

Molecular Weight:257.75
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:5
Exact Mass:257.1182566
Monoisotopic Mass:257.1182566
Topological Polar Surface Area:52.3
Heavy Atom Count:17
Complexity:227
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes