4-(2-BOC-AMINOETHYL)BENZOIC ACID

To a solution of 4-(2-aminoethyl)benzoic acid hydrochloride (10.0 g, 49.6 mmol) in a mixture of tert-butanol (liquefied, 7percent water, 150 mL) and IM sodium hydroxide (150 mL) at ambient temperature was added di-tert-buty{ dicarbonate (13.0 g, 59.5 mmol). The resulting solution was stirred at ambient temperature for 16 hours. The reaction mixture was transferred to a separatory funnel containing water (250 mL), and was washed with hexanes (2 x 250 mL). The aqueous layer was acidified to pH<2 with concentrated hydrochloric acid. The precipitate that formed was allowed to stir for several minutes, collected by filtration, washed with a small amount of water, and dried under vacuum to afford 4-(2-(tert- butoxycarbonylamino)ethyl)benzoic acid as a white powder (12.5 g, 95percent yield).p-aminoethylbenzoic acid hydrochloride (5g, MW201 .5, 24.8mmol) and NaHC010A: 4-(2-aminethyl)-benzoic acid (200 mg, 0.99 mmol) and Boc30B 4-[2-(t-Butoxycarbonylamino)ethyl]benzoic acid A mixture of 4-(2-((/ert-Butoxycarbonyl)amino)ethyl)benzoic acid (0.265 g, 1 mmol), (0108) HATU(0.494 g, 1.3 mmol) and TEA (0.202 g, 2 mmol) in dichloromethane (20 mL) was stirred at room temperature for 30 min. Then 2-(pyrrolidin-l-yl)ethanamine (0.126 g, 1.1 mmol) was added and the reaction was stirred at room temperature for 2 h. After more dichloromethane (80 mL) was added, the reaction mixture washed with water (2x20 mL). After drying with NaiSOr. removal of the solvent provided the crude product. Purification by column chromatography afforded the title compound as white solid (0.337 g, 93.2% yield). NMR (500 MHz, DMSO- d6) d: 8.47 (s, 1H), 7.78 (d, J= 8.2 Hz, 2H), 7.29 (d, J= 8.1 Hz, 2H), 6.88 (t, J= 5.3 Hz, 1H), 3.51 - 3.42 (m, 2H), 3.18 - 3.13 (m, 2H), 2.94 (br, 5H), 2.74 (t, J= 7.4 Hz, 2H), 2.69 (s, 1H), 1.81 (s, 4H), 1.36 (s, 9H).

Molecular Weight:265.30
XLogP3:2.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:6
Exact Mass:265.13140809
Monoisotopic Mass:265.13140809
Topological Polar Surface Area:75.6
Heavy Atom Count:19
Complexity:314
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes