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| | 2-Oxazolidinone, 5-(2,2-diMethyl-4H-1,3-benzodioxin-6-yl)-, (5R)- Basic information |
| Product Name: | 2-Oxazolidinone, 5-(2,2-diMethyl-4H-1,3-benzodioxin-6-yl)-, (5R)- | | Synonyms: | 2-Oxazolidinone, 5-(2,2-diMethyl-4H-1,3-benzodioxin-6-yl)-, (5R)-;(5R)-2-Oxazolidinone, 5-(2,2-diMethyl-4H-1,3-benzodioxin-6-yl);(5R)-5-(2,2-DiMethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one;(R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one;(R)-5-(2,2-DIMETHYL-4H-BENZO[D][1,3]DIOXIN-6-YL)OXAZOLIDIN-2-ONE;BNKY020-VT04;Vilanterol Impurity 29;Vilanterol internate 1 | | CAS: | 452339-73-0 | | MF: | C13H15NO4 | | MW: | 249.26 | | EINECS: | 1592732-453-0 | | Product Categories: | Intermediate;452339-73-0 | | Mol File: | 452339-73-0.mol |  |
| | 2-Oxazolidinone, 5-(2,2-diMethyl-4H-1,3-benzodioxin-6-yl)-, (5R)- Chemical Properties |
| Melting point | 160 - 163°C | | Boiling point | 489.6±45.0 °C(Predicted) | | density | 1.223±0.06 g/cm3(Predicted) | | storage temp. | Inert atmosphere,Store in freezer, under -20°C | | solubility | Chloroform (Sparingly), Methanol (Slightly) | | form | Solid | | pka | 12.29±0.40(Predicted) | | color | White to Off-White | | InChI | InChI=1S/C13H15NO4/c1-13(2)16-7-9-5-8(3-4-10(9)18-13)11-6-14-12(15)17-11/h3-5,11H,6-7H2,1-2H3,(H,14,15)/t11-/m0/s1 | | InChIKey | JUEBDVANOFZMMX-NSHDSACASA-N | | SMILES | O1[C@H](C2=CC=C3OC(C)(C)OCC3=C2)CNC1=O |
| | 2-Oxazolidinone, 5-(2,2-diMethyl-4H-1,3-benzodioxin-6-yl)-, (5R)- Usage And Synthesis |
| Uses |
(5R)-5-(2,2-diMethyl-4H-1,3-benzodioxin-6-yl)-2-Oxazolidinone (2-Oxazolidinone, 5-(2,2-diMethyl-4H-1,3-benzodioxin-6-yl)-, (5R)-) is a reagent applied in the preparation of alkyl-linked di-phenyl aminoalcohols as long-acting β2 adrenergic receptor agonist. It is used as an antedrug.
| | Synthesis |
(R)-2-amino-1-(2,2-dimethyl-4H-benzo[d][1,3]dioxin-6-yl)ethan-1-ol (29.8g, 134.0mmol, 1.0eq.) and tetrahydrofuran (300mL) were added to the reaction flask under nitrogen protection, the reaction solution was heated to 40-60°C, and N, N'- Carbonyldiimidazole (22.7 g, 140.0 mmol, 1.05 eq.).After the addition, the reaction solution was kept at a temperature of 40-60° C. and stirred until the raw material reaction was completed. After the reaction, the solution was cooled to 15-30° C., and water (400 mL) was added. Then, the mixture was continuously cooled to 0-10°C and kept stirring. The precipitated solid was filtered, and the filter cake was washed with water. The filter cake was collected and dried under reduced pressure to obtain 2-Oxazolidinone, 5-(2,2-diMethyl-4H-1,3-benzodioxin-6-yl)-, (5R)- (30 g, 120.4 mmol, 89.9% yield).
| | References | [1] Patent: CN106957313, 2017, A. Location in patent: Paragraph 0014-0015
[2] Organic and biomolecular chemistry, 2003, vol. 1, # 7, p. 1106 - 1111
[3] Patent: US2015/239862, 2015, A1. Location in patent: Paragraph 0133; 0134
[4] Patent: WO2004/22547, 2004, A1. Location in patent: Page 43-44
[5] Patent: WO2004/37773, 2004, A1. Location in patent: Page 46 |
| | 2-Oxazolidinone, 5-(2,2-diMethyl-4H-1,3-benzodioxin-6-yl)-, (5R)- Preparation Products And Raw materials |
| Raw materials | (R)-2-Amino-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol-->CarbaMic acid, [(2R)-2-(2,2-diMethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]-, 1,1-diMethylethyl ester-->1,1'-Carbonyldiimidazole-->Ethyl acetate | | Preparation Products | 2-Oxazolidinone, 3-[6-[2-[(2,6-dichlorophenyl)Methoxy]ethoxy]hexyl]-5-(2,2-diMethyl-4H-1, 3-benzodioxin-6-yl)-, (5R)--->Vilanterol Trifenatate |
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