9-Fluorenylmethyl carbazate

white powder

9-H-Fluoren-9-ylmethyl carbazate (1) (0156) To a well-stirred solution of hydrazine hydrate (19 g, 386 mmol) in 150 mL of CHSynthesis of compound 7 The hydrazine hydrate (48.5 g, 970 mmol) was dissolved in diethyl ether (200 ml).Cooling at 0 ° C, A cooling solution was obtained, and FMOC-Cl (25 g, 97 mmol) was dissolved in diethyl ether (100 ml).And added dropwise to the cooling solution, stirred for 30 minutes, and then stirred at room temperature overnight.The obtained reaction mixture A was filtered, and the obtained solid was washed with water (3×100ml).The solvent was removed to give A1 (24.1 g, 95 mmol, 98percent).At 0 °C Fmoc chloride (2 mmol, 517.4 mg) dissolved in acetonitrile (30 mL) is added to hydrazine hydrate (20 mmol, 1 g, 10 equiv) dissolved in 10 mL of a 1/1 mixture water/acetonitrile. The reaction was stirred at 0 °C for 2 h (formation of a white precipitate), then allowed to warm up to room temperature and stirred for an additional hour. The mixture was concentrated under vacuo and the precipitate was washed with water, cyclohexane, and then dried under vacuo to afford the pure title compound as a white solid (481 mg, 95percent). Mp 174 °C (lit. 172-173 °C).refPreviewPlaceHolderFmoc-CI (10 g, 38.7 MMOL) dissolved in diethyl ether (180 mL) was added dropwise to a solution of hydrazine hydrate (3.8 mL, 77 MMOL) in diethyl ether (100 mL) cooled in an ice-bath. White precipitation formed quickly. When all the FMOC-CI was added the resulting white suspension was warmed to rt. and stirred for 30 min. The white solid was isolated by filtration, washed with diethyl ether (x3) and water (x3) and dried in vacuo to give the desired product. Yield : 8 g (81percent) ; Rf = 0.2 (PE: EA 1: 1 + a few drops of acetic acid); HPLC: Rt = 4.16 min. (>99percent) ; H-NMR (DMSO-D6, 250 MHz) 8 8.34 (br, 1 H), 7.90-7. 88 (d, J = 7.3, 2H), 7.71-7. 68 (d, J = 7.3, 2H), 7.45-7. 29 (m, 4H), 4.30-4. 18 (m, 3H), 4.08 (br, 2H) ; 13C (DMSO-D6, 250 MHz) 8 158.2, 143.8, 140.7, 127.6, 127.0, 125.2, 120.0, 65.6, 46.7 ; ES-MS: mass CALCD for C15H15N202 255.1 (MH+). Found m/z 255.1.2.0 mmol of 3-phenylglutaric anhydride and 2.0 mmol of Fmoc-hydrazine are dissolved in 30 ml of THF and heated under reflux for 16 hours. The product is then extracted with 50 ml of DCM and 50 ml of 1N HCl solution and the organic phase is dried with MgSO4 and filtered off. Removal of the solvent gives 5-[N'-(9H-fluoren-9-ylmethoxycarbonyl)hydrazino]-5-oxo-3-phenylpentanoic acid. RT=10.4 (30-->80percent B, 30 min); MS (ESI): m/e=910.8 ([2M+Na]+)

Fluorescent derivatization reagent for carbohydrate

Molecular Weight:254.28
XLogP3:2.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:254.105527694
Monoisotopic Mass:254.105527694
Topological Polar Surface Area:64.4
Heavy Atom Count:19
Complexity:312
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes