BZ-OSU

General procedure: benzoic acid (0.353 g, 2.89 mmol) was dissolved in 50 mL of dry THF, and N-hydroxysuccinimide (0.40 g, 3.47 mmol) and DCC (0.776 g, 3.76 mmol) were added. The mixture was stirred at room temperature for 2 days. The soluble portion was separated from the viscous residue and the solvent was removed under reduced pressure. The residue was dissolved in CHClGeneral procedure: Benzoic acid (ring d-5, heavy isotope, d-Bz) (127 mg, 1.00 mmol) or benzoic acid (ring d-0, light isotope, Bz) (122 mg, 1.00 mmol), N-hydroxysuccinimide (230 mg, 2.00 mmol) and triethylamine (167 μL, 1.20 mmol) were dissolved in anhydrous dimethylformamide (DMF) (1 mL). After addition of dicyclohexylcarbodiimide (DCC) (206 mg, 1.20 mmol), the solution was stirred at room temperature for 3 h. The reaction mixture was filtered to remove the precipitate, and concentrated in vacuo. The resulting syrup was crystallized from isopropanol (5 mL) to yield benzoic acid N-succinimidyl ester (d-Bz labeling reagent, 184 mg, 82percent) (Bz labeling reagent, 170 mg, 78percent). Rf = 0.42 (toluene-EtOAc = 10:1); 1H-NMR (600 MHz, CDCl3): δ 2.91 (s, 4H) for the heavy isotope, δ 2.91 (s, 4H), 7.52 (dd, 2H), 7.69 (dd, 1H), 8.14 (dd, 2H) for the light isotope; 13C-NMR (125 MHz, CDCl3): δ 25.63, 124.88, 128.31, 130.13, 134.38, 161.82, 169.24 for the heavy isotope, δ 25.65, 125.08, 128.83, 130.55, 134.91, 161.84, 169.23 for the light isotope.Benzoic acid (3 g, 24.6 mmol) and N-hydroxysuccinimide (4.24 g, 36.8 mmol, 1.5 eq) were dissolved in 50 mL CHGeneral procedure: p-Fluorobenzaldehyde 1a (124.0 mg, 1.0 mmol, 1.0 equiv.) and NHSI (2b) (62.5 mg, 0.5 mmol, 0.5 equiv.) were dissolved in DEC/CHGeneral procedure: To a test tube charged with a stir bar, 0.20 mmol of1a and 0.20 mmol of BPO weresequentially added MeCN 1.0 mL and 0.20 mmol of DABCO. The resulting reactionmixture was stirred at room temperature for 3 h and diluted by addition of EtOAc, the organic layer was briefly washed by saturated aqueous sodium bicarbonatesolution, brine and dried over anhydrous sodium sulfate. The bulk solvent wasremoved in vacuo, and the residue waspurified by silica gel flash chromatography (hexane/EtOAc = 5:1) to affordproduct 2a 48.8 mg, 90percent yield.

Molecular Weight:219.19
XLogP3:0.9
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:219.05315777
Monoisotopic Mass:219.05315777
Topological Polar Surface Area:63.7
Heavy Atom Count:16
Complexity:304
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes