4-(FMOC-AMINOMETHYL)BENZOIC ACID

white powder

(4-aminomethyl)-benzoic acid (4.9 g, 1. 1 equiv. ) was dissolved in 5percent NaHCO3 150 ml in water and stirred. N- (9- Fluorenylmethoxycarbonyl) -L-proline (Fmoc, 1 equiv. , lOg) was dissolved in an equivalent amount of dioxane and added. The reaction was allowed to stir at room temperature. After two hours, 10percent citric acid in water 75 ml was added. A white solid precipitated upon addition. The solid was washed filtered and washed with hexane. The solid was dissolved in THF and allowed to dry overnight over MGSO. The following day, the solution was filtered, crystallized from THF and hexane, and placed under a drying vacuum (90percent yield). ESIMS: (M+H) + Calcd, 373.1 ; Found, 374.1.4-(Aminomethyl)benzoic acid (304 mg, 2.0 mmol) was stirred in 10percent Sodium hydrogencarbonate (sat aq, 10 ml). N-(9-Fluorenylmethoxycarbonyloxy)succinimide (680 mg, 2.0 mmol) and acetone (10 ml) was added and thick suspension was formed. Water (10 ml) was added to give an almost clear mixture that was stirred at room temperature over week-end. The mixture was washed with dichloromethane (a thick precipitate was formed in the water layer). The water layer was acidified with HCI (1 M) and extracted with dichloromethane (the precipitate moved into the dichloromethane layer). The precipitate was filtered off, dissolved in acetone and the insoluble material was filtered off. This latter filtrate was evaporated and dried on pump to yield a pure product (174 mg, 0.466 mmol, 23 percent). H NMR (400 MHz, DMSO-cfe) δ ppm 4.25 (m, 3 H) 4.38 (d, J^6.6 Hz, 2 H) 7.26 - 7.46 (m, 6 H) 7.70 (d, J=7.6 Hz, 2 H) 7.81 - 7.99 (m, 5 H) 12.85 (br. s., 1 H). 3C NMR (101 MHz, DMSO-cfe) δ ppm 43.55, 46.82, 65.33, 120.1 1 , 125.14, 126.96, 127.03, 127.59, 129.37, 140.78, 143.86, 144.90, 156.41 , 167.19.

Molecular Weight:373.4
XLogP3:4.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:6
Exact Mass:373.13140809
Monoisotopic Mass:373.13140809
Topological Polar Surface Area:75.6
Heavy Atom Count:28
Complexity:535
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes