| Identification | Back Directory | [Name]
(S)-(-)-4-ISOBUTYLOXAZOLIDINE-2,5-DIONE | [CAS]
3190-70-3 | [Synonyms]
Leu-NCA
L-Leu-NCA
L-Leucine NCA
L-Leucine N-Carboxanhydride
L-Leucine N-carboxyanhydride
N-Carboxy-L-leucine anhydride
(S)-4-ISOBUTYL-OXAZOLIDINE-2,5-DIONE
(4S)-4-Isobutyloxazolidine-2,5-dione
(S)-(-)-4-ISOBUTYLOXAZOLIDINE-2,5-DIONE
(S)-4β-(2-Methylpropyl)-2,5-oxazolidinedione
4-(2-methylpropyl)-1,3-oxazolidine-2,5-dione
(4S)-4β-(2-Methylpropyl)oxazolidine-2,5-dione
2,5-Oxazolidinedione, 4-(2-methylpropyl)-, (4S)-
(S)-4-Isobutyloxazolidine-2,5-dione(S)-4-Isobutyloxazolidine-2,5-dione | [EINECS(EC#)]
221-692-2 | [Molecular Formula]
C7H11NO3 | [MDL Number]
MFCD03411292 | [MOL File]
3190-70-3.mol | [Molecular Weight]
157.17 |
| Chemical Properties | Back Directory | [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 Rotation]
Consistent with structure |
| Hazard Information | Back Directory | [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 |
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