(S)-(-)-4-ISOBUTYLOXAZOLIDINE-2,5-DIONE Chemical Properties

Melting point:

76-77°C

Density 

1.124±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

9.38±0.40(Predicted)

Appearance

White to off-white Solid

optical activity

Consistent with structure

Safety Information

Safety Statements 

22-24/25

HS Code 

2934999090

MSDS

• Language:English Provider:ALFA

(S)-(-)-4-ISOBUTYLOXAZOLIDINE-2,5-DIONE Usage And Synthesis

Uses

N-Carboxyleucine Anhydride is a reagent in the synthesis of hybrid polypeptide micelles which are used to load indocyanine green dyes into lab rats for tumor imaging and photothermal effect studies.

Synthesis

General procedure for the synthesis of (S)-4-isobutyloxazolidine-2,5-dione from phosgene and L-leucine: L-leucine amide (HO-Leu-NH2, 10.0 g, 76.2 mmol) was suspended in 150 mL of anhydrous tetrahydrofuran (THF), and heated to 50 °C. A 20% phosgene solution of toluene (76.0 mL, 152.4 mmol) was slowly added to the amino acid suspension. After about 1 hour, the amino acids were completely dissolved to form a clarified solution. The reaction solution was concentrated on a rotary evaporator, transferred to a beaker, and the product was precipitated by the addition of hexane. The white solid was separated by filtration and dissolved in toluene. The toluene solution was filtered through a bed of diatomaceous earth to remove insoluble impurities. Excess hexane was added to the filtrate to precipitate the product again. N-carboxy-L-leucine anhydride (Leu NCA) was obtained by filtration separation and dried under vacuum. 9.0 g (75% yield) of Leu NCA was finally obtained as a white crystalline solid. Its 1H NMR (d6-DMSO) data were as follows: δ 9.13 (1H), 4.44 (1H), 1.74 (1H), 1.55 (2H), 0.90 (6H) ppm.

References

[1] Advanced Synthesis and Catalysis, 2004, vol. 346, # 9-10, p. 1247 - 1249
[2] Patent: US2008/274173, 2008, A1. Location in patent: Page/Page column 94
[3] Journal of the Chemical Society, 1950, p. 3222,3225
[4] Patent: US2789973, 1950,
[5] Nippon Kagaku Zasshi, 1956, vol. 77, p. 44,46

(S)-(-)-4-ISOBUTYLOXAZOLIDINE-2,5-DIONE(3190-70-3)Related Product Information

• 4-isobutyloxazolidine-2,5-dione
• (S)-4-Isobutyl-2-Oxazolidinone
• DL-4-ISOBUTYLOXAZOLIDINE-2,5-DIONE,(R,S)-4-ISOBUTYLOXAZOLIDINE-2,5-DIONE
• NALPHA-9-Fluorenylmethoxycarbonyl-L-leucine N-carboxylic anhydride
• Z-L-Leucine N-carboxyanhydride
• N-tert-Butoxycarbonyl-L-leucine N-carboxylic anhydride
• (S)-(-)-4-ISOBUTYLOXAZOLIDINE-2,5-DIONE