(S)-4-Methyl-2,5-oxazolidonedione synthesis

10synthesis methods

Product Name:(S)-4-Methyl-2,5-oxazolidonedione
CAS Number:2224-52-4
Molecular formula:C4H5NO3
Molecular Weight:115.09

L-alanine (20.0 g, 0.224 mol) and triphosgene (53.4 g, 0.180 mol) were suspended in 400.0 mL of dry THF bubbled with nitrogen flux in a flame-dried three-neck flask. The mixture was stirred at 60 °C for 2 h before further bubbling with nitrogen flux for 30 min. After that, the solution was precipitated in 1000.0 mL of n-hexane and stored at -20 °C. The supernatant was removed, and the residues were collected and dissolved in 200.0 mL of ethyl acetate, before two washings with 100.0mL of ice-cold water and one washing with 100.0 mL of 0.5% NaHCO3 ice-cold aqueous solution. The organic phase was then dried over anhydrous MgSO4 and evaporated to obtain 15.5 g of L-Ala NCA ((S)-4-Methyl-2,5-oxazolidonedione). The yield of L-Ala NCA was 77.5%.

56-41-7 Synthesis

56-41-7
833 suppliers
$5.00/5g

32315-10-9 Synthesis

32315-10-9
437 suppliers
$10.00/1g

2224-52-4
156 suppliers
$11.00/250mg

Yield:2224-52-4 77.5%

Reaction Conditions:

in tetrahydrofuran at 60; for 2.5 h;Inert atmosphere;

Steps:

Synthesis of L-Ala NCA
L-alanine (20.0 g, 0.224 mol) and triphosgene (53.4 g, 0.180 mol) were suspended in 400.0 mL ofdry THF bubbled with nitrogen flux in a flame-dried three-neck flask. The mixture was stirred at 60 °C for 2 h before further bubbling with nitrogen flux for 30 min. After that, the solution was precipitated in 1000.0 mL of n-hexane and stored at -20 °C. The supernatant was removed, and the residues were collected and dissolved in 200.0 mL of ethyl acetate, prior to two washings with 100.0mL of ice-cold water and one washing with 100.0 mL of 0.5% NaHCO3 ice-cold aqueous solution. The organic phase was then dried over anhydrous MgSO4 and evaporated to obtain 15.5 g of L-Ala NCA. The yield of L-Ala NCA was 77.5%.

References:

Han, Jiandong;Zhao, Xingyu;Xu, Weiguo;Wang, Wei;Han, Yuping;Feng, Xiangru [Molecules,2018,vol. 23,# 5,art. no. 1017] Location in patent:supporting information

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