BOC-(4-AMINOPHENYL)ACETICACID

White crystalline powder

General procedure: 2-(4-((tert-Butoxycarbonyl)amino)phenyl)acetic Acid (5). A solution of 4-aminophenylacetic acid (4, 4 g, 26.46 mmol, 1 equiv.) in a mixture of dioxane (52 mL) and water (52 mL), and sodium carbonate(2.8 g, 26.42 mmol, 1 equiv., in 26 mL of water) was stirred and cooled in an ice bath. Di-tert-butyldicarbonate (BOC-anhydride, 6.24 g, 28.59 mmol, 1.1 equiv.) was added in one portion, and stirringwas continued at room temperature for 4 h. The dioxane was removed in vacuo and the aqueouslayer chilled, covered with a layer of ethyl acetate, and acidified to pH 4 with dilute KHSO4. This wasfollowed by extraction (ethyl acetate) and purification (1:1:1) of ethyl acetate–hexane–acetic acid; ethylacetate) to yield the compound 5 (Scheme 7; 7.07 g; 94percent) as a white solid. 1H-NMR (300 MHz, CDCl3):7.29 (d, J = 8.40 Hz, 2H), 7.19 (d, J = 8.47 Hz, 2H), 3.70 (s, 1H), 3.58 (s, 2H), 1.52 (s, 9H).2-(4- Aminophenyl)acetic acid (2.0 g, 13.2 mmol) and sodium carbonate (1.4 g, 13.2 mmol) were placed in a round-bottomed flask and dissolved in a mixture of water (25 mL) and 1, 4- dioxane (25 mL). The reaction was cooled to 0 °C and then di-fert-butyl dicarbonate (3.2 g, 14.6 mmol) was added to the reaction in one portion. The reaction was allowed to warm to RT and then stirred for 4h. After the reaction was complete as evidenced by TLC, the 1, 4- dioxane was removed in vacuo and the pH of the remaining aqueous solution was adjusted to approximately 4 with IN HC1. The organic products were extracted with EtOAc (3 x 30 mL), washed with brine (20 mL), dried with anhydrous NaTo a solution of 3-(4-aminophenyl) acetic acid (5.00 g, 33 mmol) in aqueous 0.2N sodium hydroxide (40 ml) was added di-tert-butyl dicarbonate (7.22 g, 33mmol) and the reaction mixture stirred at RT overnight. The reaction was acidified to pH 2 with 1M HCI and extracted with EtOAc (3 x 50 ml). The combined organic extracts were washed with

Molecular Weight:251.28
XLogP3:1.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:251.11575802
Monoisotopic Mass:251.11575802
Topological Polar Surface Area:75.6
Heavy Atom Count:18
Complexity:301
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes