| Identification | Back Directory | [Name]
5-FORMYLISOXAZOLE | [CAS]
16401-14-2 | [Synonyms]
5-FORMYLISOXAZOLE
ISOXAZOLE-5-CARBALDEHYDE
5-ISOXAZOLECARBOXALDEHYDE
Isoxazole-5-carboxaldehyde
1,2-oxazole-5-carbaldehyde | [Molecular Formula]
C4H3NO2 | [MDL Number]
MFCD07778412 | [MOL File]
16401-14-2.mol | [Molecular Weight]
97.07 |
| Chemical Properties | Back Directory | [Boiling point ]
212℃ | [density ]
1.258 | [Fp ]
82℃ | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [pka]
-3.78±0.50(Predicted) | [Appearance]
White to off-white Solid |
| Hazard Information | Back Directory | [Uses]
5-Isoxazolecarbaldehyde is the derivative of 5-Isoxazolecarboxylic Acid, which is used as a reagent in the synthesis of N-(benzo[1,2,3]triazol-1-yl)-N-((benzyl)acetamido)phenyl carboxamides as severe acute respiratory syndrome coronavirus (SARS-CoV) 3CLpro inhibitors. 5-Isoxazolecarboxylic Acid is also used as a reagent in the synthesis of TC-6683, a α4β2 nicotinic acetylcholine receptor agonist for treatment of cognitive disorders. | [Synthesis]
Step 2: Synthesis of isoxazole-5-carbaldehyde
In a round bottom flask, isoxazol-5-yl-methanol (511 mg, 5.16 mmol) was dissolved in dichloromethane (30 mL). Dess-Martin periodate (2.3 g, 5.41 mmol) was added and the reaction mixture was stirred for 1.5 h at room temperature. Upon termination of the reaction, 50 mL of 10% aqueous Na2S2O3 and saturated aqueous NaHCO3 were added, followed by extraction with dichloromethane (2 x 30 mL). The organic layer was washed sequentially with saturated NaHCO3 aqueous solution, water and brine. The aqueous layer was back-extracted with dichloromethane. The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography using EtOAc/hexane (gradient 0-40% EtOAc) as eluent to afford 226 mg (45% yield) of isoxazole-5-carbaldehyde as a colorless oil.1H NMR (CDCl3, 300 MHz) δ (ppm): 10.05 (s, 1H), 8.44 (d, J = 1.9 Hz, 1H). 7.02 (d, J = 1.9 Hz, 1H). | [References]
[1] Patent: WO2013/30138, 2013, A1. Location in patent: Page/Page column 154
[2] Tetrahedron, 1967, vol. 23, p. 4697 - 4707 |
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