(4S)-(+)-4-Benzyl-3-propionyl-2-oxazolidinone CAS 101711-78-8
(4S)-(+)-4-Benzyl-3-propionyl-2-oxazolidinone Basic information
| Product Name: | (4S)-(+)-4-Benzyl-3-propionyl-2-oxazolidinone |
| Synonyms: | N-PROPIONYL-(4S)-BENZYL-2-OXAZOLIDINONE;N-3-PROPIONYL-(4S)-BENZYL-2-OXAZOLIDINONE;(S)-(+)-4-BENZYL-3-PROPIONYL-2-OXAZOLIDINONE;(S)-4-BENZYL-3-PROPIONYL-2-OXAZOLIDINONE;(S)-(+)-4-BENZYL-3-PROPIONYL-2-OXALIDINONE;(S)-(+)-4-BENZYL-3-PROPIONYL-2-OXAZOLIDI N-ONE, 99% (99% EE/HPLC);(4s)-(+)-benzyl-3-propionyl-2-oxazolidinone;(S)-(+)-4-Benzyl-3-propionyl-2-oxazolidinone,99% |
| CAS: | 101711-78-8 |
| MF: | C13H15NO3 |
| MW: | 233.26 |
| EINECS: | 202-303-5 |
| Product Categories: | Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Asymmetric Synthesis;Chiral Auxiliaries;Oxazolidinone Derivatives;Aromatics;Oxazolidinone;API intermediates;Asymmetric Synthesis;Chiral Building Blocks;Glycidyl Compounds, etc. (Chiral);Synthetic Organic Chemistry;Peptide |
| Mol File: | 101711-78-8.mol |
(4S)-(+)-4-Benzyl-3-propionyl-2-oxazolidinone Chemical Properties
| Melting point | 42-44 °C |
| alpha | 97 º (c=1, EtOH) |
| Boiling point | 375.51°C (rough estimate) |
| density | 1.1475 (rough estimate) |
| refractive index | 103 ° (C=1, EtOH) |
| storage temp. | Inert atmosphere,Room Temperature |
| solubility | Chloroform, Methanol |
| pka | -2.35±0.40(Predicted) |
| form | Solid |
| color | Off-White to Pale Yellow |
| Optical Rotation | [α]20/D +97°, 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-/m0/s1 |
| InChIKey | WHOBYFHKONUTMW-NSHDSACASA-N |
| SMILES | O1C[C@H](CC2=CC=CC=C2)N(C(=O)CC)C1=O |
| CAS DataBase Reference | 101711-78-8(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi,Xn |
| Risk Statements | 36/37/38-20/21/22-43 |
| Safety Statements | 37/39-26-36-36/37 |
| WGK Germany | 3 |
| HS Code | 29349990 |
| Storage Class | 11 - Combustible Solids |
| Chemical Properties | Colourless Solid |
| Uses | Versatile chiral auxiliary for asymmetric synthesis. |
| Uses | Intermediate in the preparation of Albaconazole. |
| Synthesis | 90719-32-7 79-03-8 131685-53-5 Under nitrogen atmosphere, (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 dropwise 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, and 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): δ7.33 (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, 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 |
(4S)-(+)-4-Benzyl-3-propionyl-2-oxazolidinone Preparation Products And Raw materials
| Raw materials | (S)-4-Benzyl-2-oxazolidinone-->Propionic-2,3-14C1 acid (8CI)-->Propionic anhydride-->Propionyl chloride-->Hexane-->Tetrahydrofuran-->n-Butyllithium |
