FMOC-6-AMINOHEXANOIC ACID

White powder

To a solution of 389 mg (2.96 mmol) 6-aminohexanoic acid in 20 mL acetone/water (1:1), 1.00 g(2.96 mmol) FmocOSuc and 250 mg (2.96 mmol) NaHCO3 were added. The suspension was stirred at rt for 3 h. Acetone was removed at reduced pressure and 20 mL of DCM were added to the residue. The precipitated solid was removed by filtration. The organic phase was washed with 10 mL of 0.1 M HCl and 10 mL ofwater. The solution was dried over Na2SO4, the solvent removed at reduced pressure and the residue was dried in vacuo, yielding 747 mg (71percent) of a colourless solid.6-Amino-hexanoic acid (13.1 g, 100 mmoL) was dissolved in 10percent aqueous Na2CO3 solution (300 mL), then dioxane (200 mL) was added to the above solution. Fmoc-CI (26 g, 110 mmoL) was added to the above mixture portion-wise, and the resultant reaction mixture was stirring for 12h. The mixture was extracted with ether (150 mL X 2), and the aqueous portion was acidified by 6N HCI. The mixture was filtered, and the solid was washed with water and dried to give 6- (9H-Fluoren-9-ylmethoxycarbonylamino)-hexanoic acid as a white solid (31 g, 81 percent). 6- (9H-Fluoren-9-ylmethoxycarbonylamino)-hexanoic acid (9.17 g, 25 mmoL) and 0- (2, 4- dimethoxy-benzyl)-hydroxylamine (36 g, 26 mmoL) were dissolved in DCM (250 mL), then DCC (6.18 g, 30 mmoL) was added ortion-wise. The resultant mixture was stirred for 3h at room temperature, then cooled to 0°C, filtered, and washed with DCM. The organic solution was evaporated to dryness to give the crude [5- (2, 4-dimethoxy- benzyloxycarbamoyl)-pentyl]-carbamic acid 9H-fluoren-9-ylmethyl ester. The crude ester was reacted with piperidine (5 mL) in MeOH (150 mL) at room temperature for12 h. The solution was evaporated and the residue was purified by flash chromatography (silica, EtOAc: MeOH = 5: 1). 6-Amino-hexanoic acid (2, 4-dimethoxy- benzyloxy)-amide was obtained as a white solid (4.15 g, 56percent).

Molecular Weight:353.4
XLogP3:3.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:9
Exact Mass:353.16270821
Monoisotopic Mass:353.16270821
Topological Polar Surface Area:75.6
Heavy Atom Count:26
Complexity:459
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes