ChemicalBook CAS DataBase List 4-isobutyloxazolidine-2,5-dione

4-isobutyloxazolidine-2,5-dione synthesis

7synthesis methods

Product Name:4-isobutyloxazolidine-2,5-dione
CAS Number:51248-35-2
Molecular formula:C7H11NO3
Molecular Weight:157.17

A solution of phosgene(12.5% in toluene, 25 mL, 31.6 mmol) was added to a suspension of l-leucine (1.31 g, 10 mmol) in dioxane (30 mL) and ethyl acetate (25 mL) at 40 ℃ under a static atmosphere of nitrogen. After 4 h, the leucine had dissolved and then the excess phosgene was removed in a stream of nitrogen. The solvent was removed at 40 ℃ in vacuo and the residue was recrystallized from diethyl ether/light petroleum (bp 40–60 ℃) to yield colorless needles of 4-(2-methylpropyl)oxazolidine-2,5-dione (1.01 g, 69%).

32315-10-9 Synthesis

32315-10-9
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328-39-2
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51248-35-2
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$22.00/1g

Yield:51248-35-2 95%

Reaction Conditions:

with α-pinene in tetrahydrofuran;Inert atmosphere;

Steps:

3 2.3. Synthesis of leucine N-carboxyanhydride (Leu-NCA)

This NCA monomer was prepared as described by Smeets et al. [17] Leucine (8.02 g, 61.0 mmol) was suspended in anhydrous THF (100 mL).
α-pinene (25.0 mL, 157 mmol) and solid triphosgene (6.70 g, 22.2 mmol) were sequentially added under nitrogen atmosphere. The suspension was heated under reflux at 64 °C until it turned yellow and clear (~ 30 min).
The solution was then cooled down to room temperature and bubbled with nitrogen following the same procedure described above for the synthesis of γ-benzyl-glutamic acid NCA. The solvent was then removed under reduced pressure to yield a yellow oily residue.
Petroleum ether (300 mL) was added to induce the precipitation of Leu-NCA as a white solid.
This precipitate was filtered, washed with ice-cold petroleum ether (3 * 25 mL), and dried under reduced pressure, to give leucine N-carboxyanhydride (Leu-NCA) as a white solid (7.65 g, 48.6 mmol) with a recovery yield of 95% (mol/mol).
¹H NMR (400 MHz, CDCl₃): δ 6.43 (bs, 1H, NHCH) 4.33 (dd, J = 8.9, 4.0 Hz, 1H, NHCH), 1.82 (m, 2H, CH₂CH), 1.68 (m, 1H, CH(CH₃)₂), 0.99 (m, 6H, CH(CH₃)₂).
¹³C NMR (101 MHz, CDCl₃): δ 170.25 (1C, C(O)CH), 153.38 (1C, C(O)NH), 56.33 (1C, CHCH₂), 40.88 (1C, CH₂CH), 25.06 (1C, CH(CH₃)₂), 22.79 and 21.59 (2C, CH(CH₃)₂).
FT-IR: υ 2960, 1798, 1750, 1468, 1117, 1079 cm^-1.

References:

Brunato, Silvia;Mastrotto, Francesca;Bellato, Federica;Bastiancich, Chiara;Travanut, Alessandra;Garofalo, Mariangela;Mantovani, Giuseppe;Alexander, Cameron;Preat, Veronique;Salmaso, Stefano;Caliceti, Paolo [Journal of Controlled Release,2021,vol. 335,p. 21 - 37]

61-90-5 Synthesis