|
|
| | (R)-(-)-4-BENZYL-3-PROPIONYL-2-OXAZOLIDINONE Basic information |
| | (R)-(-)-4-BENZYL-3-PROPIONYL-2-OXAZOLIDINONE Chemical Properties |
| Melting point | 45 °C | | Boiling point | 396.6±11.0 °C(Predicted) | | density | 1.206±0.06 g/cm3(Predicted) | | refractive index | -103 ° (C=1, EtOH) | | storage temp. | Inert atmosphere,Room Temperature | | solubility | Chloroform, Ethanol | | pka | -2.35±0.40(Predicted) | | form | Solid | | color | Off-White | | Optical Rotation | [α]20/D 102°, c = 1 in ethanol | | InChI | InChI=1S/C13H15NO3/c1-2-12(15)14-11(9-17-13(14)16)8-10-6-4-3-5-7-10/h3-7,11H,2,8-9H2,1H3/t11-/m1/s1 | | InChIKey | WHOBYFHKONUTMW-LLVKDONJSA-N | | SMILES | O1C[C@@H](CC2=CC=CC=C2)N(C(=O)CC)C1=O | | CAS DataBase Reference | 131685-53-5(CAS DataBase Reference) |
| | (R)-(-)-4-BENZYL-3-PROPIONYL-2-OXAZOLIDINONE Usage And Synthesis |
| Chemical Properties | white to light yellow crystal powde | | Uses | (R)-(-)-4-BENZYL-3-PROPIONYL-2-OXAZOLIDINONE is a oxazolidinone derivative used in the preparation of anisomycin analogues as activators of the JNK/SAPK1 and p38/SAPK2 pathways. | | Uses | (R)-()-4-Benzyl-3-propionyl-2-oxazolidinone can be used as a building block for the preparation of methyl 3-[(S)-3-((R)-4-benzyl-2-oxooxazolidin-3-yl)-2-methyl-3-oxopropyl]benzoate by treating with strong base followed by the addition of methyl 3-bromomethyl benzoate. | | General Description | (R)-()-4-Benzyl-3-propionyl-2-oxazolidinone is used as a building block in organic synthesis for the preparation of oxazolidinone derivatives. | | Synthesis | Under nitrogen protection, (S)-4-benzyl-2-azolidinone (800 mg, 4.5 mmol) was dissolved in a dry reaction vial of anhydrous tetrahydrofuran (30 mL) and cooled to -78 °C in a dry ice/acetone bath. A hexane solution of 1.6 M n-butyllithium (5.0 mmol, 3.1 mL) was added slowly and dropwise over 3 min. After stirring for 30 min, propionyl chloride (5.0 mmol, 0.43 mL) was added slowly over 3 min. The reaction solution was slowly warmed to room temperature over 14 h. The reaction was subsequently quenched by the addition of saturated ammonium chloride solution (10 mL) and water (30 mL). The aqueous layer was extracted with ethyl acetate (3 x 40 mL), the organic phases were combined and dried over anhydrous magnesium sulfate. The organic phase was concentrated under reduced pressure to afford (R)-(-)-benzyl-3-propionyl-2-oxazolidinone (oil, 1.0 g, 96% yield) with >95% purity by HPLC.1H NMR (500 MHz, CDCl3): δ 7.33 (dd, J1 = 7.4 Hz, J2 = 7.6 Hz, 2H), 7.29 (d, J = 6.9 Hz, 1H) ), 7.21 (d, J = 7.4 Hz, 2H), 4.67 (m, 1H), 4.18 (m, 2H), 3.31 (dd, J1 = 13.3 Hz, J2 = 3.2 Hz, 1H), 2.96 (m, 2H), 2.77 (dd, J1 = 13.3 Hz, J2 = 3.7 Hz, 1H), 1.21 (t, J = 7.4 Hz, 1H). 3H). | | References | [1] Chemistry - An Asian Journal, 2011, vol. 6, # 7, p. 1791 - 1799
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 1, p. 144 - 148
[3] Journal of Organic Chemistry, 2008, vol. 73, # 8, p. 3292 - 3294
[4] Angewandte Chemie - International Edition, 2016, vol. 55, # 13, p. 4252 - 4255
[5] Angew. Chem., 2016, vol. 128, # 13, p. 4324 - 4327,4 |
| | (R)-(-)-4-BENZYL-3-PROPIONYL-2-OXAZOLIDINONE Preparation Products And Raw materials |
|