ChemicalBook CAS DataBase List Fmoc-L-Lys(Dde)-OH

Fmoc-L-Lys(Dde)-OH synthesis

4synthesis methods

Product Name:Fmoc-L-Lys(Dde)-OH
CAS Number:150629-67-7
Molecular formula:C31H36N2O6
Molecular Weight:532.63

94142-97-9 Synthesis

94142-97-9
103 suppliers
$22.00/1g

71989-26-9 Synthesis

71989-26-9
475 suppliers
$5.00/1g

150629-67-7
219 suppliers
$6.00/100mg

Yield:150629-67-7 41%

Reaction Conditions:

Stage #1:Fmoc-Lys(tert-butoxycarbonyl) with hydrogenchloride in 1,4-dioxane at 20; for 2 h;
Stage #2:2-(1-hydroxyethylidene)-5,5-dimethylcyclohexane-1,3-dione with N-ethyl-N,N-diisopropylamine in ethanol for 17 h;Reflux;

Steps:

4.1.4. Synthesis of Fmoc-Lys(Dde)-OH
Fmoc-Lys(Boc)-OH (5.66 g, 12.1 mmol) was dissolved in 4 M HCl/dioxane (120 mL), and stirred at room temperature for 2 h to remove the side-chain Boc group. The solvent was removed under reduced pressure. The resulting residue was dissolved in EtOH(60 mL), and then 2-acetyldimedone (3.36 g, 18.4 mmol) and DIPEA (6.2 mL, 35.6 mmol) were added. The reaction mixture was refluxed for 17 h. After cooling to room temperature, the solvent was removed under reduced pressure. The residue was dissolved in AcOEt (300 mL) and washed with 1 M HCl (100 mL) and brine (100 mL), dried over Na2SO4, filtered, and concentrated. The resulting residue was purified by silica gel column chromatography(0.5%-3% MeOH/DCM) to give Fmoc-Lys(Dde)-OH (2.64 g,41%) as a white solid. Spectroscopic data are identical to the published data.34 ¹H NMR (500 MHz, CDCl3): d 13.31 (brs, 1H), 7.75(d, J = 7.8 Hz, 2H), 7.59 (t, J = 7.8 Hz, 2H), 7.38 (t, J = 7.8 Hz, 2H),7.31-7.28 (m, 2H), 5.73 (d, J = 8.0 Hz, 1H), 4.48-4.45 (m, 1H),4.37 (d, J = 7.1 Hz, 2H), 4.20 (t, J = 7.1 Hz, 1H), 3.43-3.40 (m, 2H),2.55 (s, 3H), 2.36 (s, 4H), 2.00-1.50 (m, 6H), 1.01 (s, 6H). HR-MS(m/z, FAB): calcd for C31H37N2O6 ([M + H]+), 533.2652; found,533.2643.

References:

Amano, Yuichi;Umezawa, Naoki;Sato, Shin;Watanabe, Hisami;Umehara, Takashi;Higuchi, Tsunehiko [Bioorganic and Medicinal Chemistry,2017,vol. 25,# 3,p. 1227 - 1234]

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1755-15-3 Synthesis