ChemicalBook CAS DataBase List Nalpha-FMOC-L-Glutamine

Nalpha-FMOC-L-Glutamine synthesis

6synthesis methods

Product Name:Nalpha-FMOC-L-Glutamine
CAS Number:71989-20-3
Molecular formula:C20H20N2O5
Molecular Weight:368.38

56-85-9

N-(9-Fluorenylmethoxycarbonyloxy)succinimide

82911-69-1

71989-20-3

To a stirred solution of L-glutamine (1.75 g, 12 mmol) and sodium carbonate (1.27 g, 12 mmol) in 30 mL of water, a solution of 9-fluorenylmethyl-N-succinimidyl carbonate (Fmoc-OSu, 3.0 g, 8.9 mmol) dissolved in 60 mL of tetrahydrofuran (THF) was slowly added. The reaction mixture was stirred overnight at room temperature. Subsequently, THF was removed by distillation under reduced pressure. the residue was diluted with 100 mL of 1N hydrochloric acid and the precipitated white solid was collected by filtration. The solid was further recrystallized in a mixed aqueous solution of DMF with 0.1 N hydrochloric acid to afford the target product (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-amino-5-oxopentanoic acid as a white powder (2.76 g, 84% yield). The product was characterized by 1H-NMR (90 MHz, DMSO-d6) with chemical shifts of 12.47 (1H, s), 7.89-7.20 (10H, m), 6.68 (1H, s, br), 4.22-3.90 (4H, m), and 2.25-1.86 (4H, m).

56-85-9 Synthesis

56-85-9
1062 suppliers
$5.00/5g

82911-69-1 Synthesis

82911-69-1
648 suppliers
$7.00/25g

71989-20-3
362 suppliers
$6.00/5g

Yield:71989-20-3 84%

Reaction Conditions:

with sodium carbonate in tetrahydrofuran;water

Steps:

To a stirred solution of L-glutamine (1.75 g, 12 mmole) and sodium carbonate (1.27 g, 12 mmole) in 30 ml of water, was added a solution of Fmoc-OSu (3.0 g, 8.9 mmole) in 60 ml of THF. After stirring overnight the mixture was concentrated under reduced pressure to remove the THF. The residue was diluted with 100 ml of 1 N hydrochloric acid . The white solid was collected by filtration and recrystallized in DMF-0.1 N hydrochloric acid aqueous solution to afford a white powder (38, 2.76 g). Yield: 84%. ¹H-NMR (90 MHz, DMSO-d6) ppm: 12.47 (1H, s), 7.89-7.20 (10 H, m), 6.68 (1H, s, br), 4.22-3.90 (4H, m), and 2.25-1.86 (4H, m).

References:

M. Martin, Lenore;Hu, Bi-Huang US2006/161007, 2006, A1 Location in patent:Page/Page column 12

FullText

132327-80-1 Synthesis