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| | (4S)-3-[(5R)-5-(4-FLUOROPHENYL)-5-HYDROXYPENTANOYL]-4-PHENYL-1,3-OXAZOLIDIN-2-ONE Basic information |
| | (4S)-3-[(5R)-5-(4-FLUOROPHENYL)-5-HYDROXYPENTANOYL]-4-PHENYL-1,3-OXAZOLIDIN-2-ONE Chemical Properties |
| Boiling point | 572.7±50.0 °C(Predicted) | | density | 1.297 | | storage temp. | 2-8°C | | solubility | Chloroform (Sparingly), Methanol (Slightly) | | form | Solid | | pka | 14.17±0.20(Predicted) | | color | White to Off-White | | InChI | InChI=1S/C20H20FNO4/c21-16-11-9-15(10-12-16)18(23)7-4-8-19(24)22-17(13-26-20(22)25)14-5-2-1-3-6-14/h1-3,5-6,9-12,17-18,23H,4,7-8,13H2/t17-,18+/m1/s1 | | InChIKey | AVAZNWOHQJYCEL-MSOLQXFVSA-N | | SMILES | O1C[C@H](C2=CC=CC=C2)N(C(=O)CCC[C@@H](C2=CC=C(F)C=C2)O)C1=O |
| | (4S)-3-[(5R)-5-(4-FLUOROPHENYL)-5-HYDROXYPENTANOYL]-4-PHENYL-1,3-OXAZOLIDIN-2-ONE Usage And Synthesis |
| Description | (4S)-3-[(5R)-5-(4-FLUOROPHENYL)-5-HYDROXYPENTANOYL]-4-PHENYL-1, 3-OXAZOLIDIN-2-ONE is a derivative of 2-oxazolidine, which is an effective antimicrobial. It can be used as a pharmaceutical intermediate for the preparation of ezetimibe which is a drug used to lower the patients’ plasma cholesterol levels. | | Chemical Properties | Solid | | Uses | 3-[(5S)-(4-Fluorophenyl)-5-hydroxypentanoyl]-(4S)-phenyl-1,3-oxazolidin-2-one is an intermediate of Ezetimibe (E975000, E975002), an antihyperlipoproteinemic. A cholesterol absorption inhibitor. | | Synthesis | A process for synthesis of (4S)-3-[(5R)-5-(4-FLUOROPHENYL)-5-HYDROXYPENTANOYL]-4-PHENYL-1,3-OXAZOLIDIN-2-ONE comprising of resolution of 4S- phenyl -3-[(5RS)-5-(4-fluorophenyl)-5-hydroxypentanoyl] -1,3 oxazolidin 2-one by selective esterification of 4S-phenyl -3-[(5R)-5-(4-fluorophenyl)-5-hydroxypentanoyl] -1,3 oxazolidin 2-one using appropriate esterification reagent in an organic solvent in presence of Lipase enzyme at a temperature ranging from 0° to 100°C, and further isolation. | | References | http://www.cphi-online.com/ezetimibe-intermediate-4s3-prod587443.html
https://en.wikipedia.org/wiki/2-Oxazolidone |
| | (4S)-3-[(5R)-5-(4-FLUOROPHENYL)-5-HYDROXYPENTANOYL]-4-PHENYL-1,3-OXAZOLIDIN-2-ONE Preparation Products And Raw materials |
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