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| | 8-acetyl-6-(benzyloxy)-2H-benzo[b][1,4]oxazin-3(4H)-one Basic information |
| Product Name: | 8-acetyl-6-(benzyloxy)-2H-benzo[b][1,4]oxazin-3(4H)-one | | Synonyms: | 8-acetyl-6-phenylmethoxy-4H-1,4-benzoxazin-3-one;8-acetyl-6-(benzyloxy)-2H-benzo[b][1,4]oxazin-3(4H)-one;2H-1,4-Benzoxazin-3(4H)-one, 8-acetyl-6-(phenylMethoxy)-;8-acetyl-6-benzyloxy-4H-benzo[1,4]oxazin-3-one;8-acetyl-6-(phenylmethoxy)-2H-1,4-benzoxazin-3(4H)-one;8-acetyl-6-benzyloxy-4H-1,4-benzoxazin-3-one;8- Acetyl-6 - (benzoxy) -2H- Benzo [b] [1,4] oxazine -3 (4H) -ONE;8-acetyl-6-(benzyloxy)-3,4-dihydro-2H-1,4-benzoxazin-3-one | | CAS: | 869478-09-1 | | MF: | C17H15NO4 | | MW: | 297.31 | | EINECS: | | | Product Categories: | | | Mol File: | 869478-09-1.mol | ![8-acetyl-6-(benzyloxy)-2H-benzo[b][1,4]oxazin-3(4H)-one Structure](CAS/GIF/869478-09-1.gif) |
| | 8-acetyl-6-(benzyloxy)-2H-benzo[b][1,4]oxazin-3(4H)-one Chemical Properties |
| Boiling point | 517.2±50.0 °C(Predicted) | | density | 1.259±0.06 g/cm3(Predicted) | | storage temp. | Inert atmosphere,Room Temperature | | solubility | Chloroform, DCM, Methanol | | pka | 11.84±0.20(Predicted) | | form | Solid | | color | Beige | | InChI | InChI=1S/C17H15NO4/c1-11(19)14-7-13(21-9-12-5-3-2-4-6-12)8-15-17(14)22-10-16(20)18-15/h2-8H,9-10H2,1H3,(H,18,20) | | InChIKey | URTYAHMRXXVHKS-UHFFFAOYSA-N | | SMILES | O1C2=C(C(C)=O)C=C(OCC3=CC=CC=C3)C=C2NC(=O)C1 |
| | 8-acetyl-6-(benzyloxy)-2H-benzo[b][1,4]oxazin-3(4H)-one Usage And Synthesis |
| Uses | 8-Acetyl-6-benzyloxy-4H-benzo[1,4]oxazin-3-one is an intermediate in the synthesis of Olodaterol (O262000), a novel inhaled β2-adrenoceptor agonist with a 24h bronchodilatory efficacy. | | Synthesis | The general procedure for the synthesis of 8-acetyl-6-(benzyloxy)-2H-benzo[b][1,4]oxazin-3(4H)-ones from 1-(3-amino-5-(benzyloxy)-2-hydroxyphenyl)ethanone and chloroacetyl chloride is as follows: 21.0 mL (258 mmol) of chloroacetyl chloride was slowly added dropwise under ice-bath cooling to a mixture containing 60.0 g (233 mmol) 1-(3-amino-5-benzyloxy-2-hydroxyphenyl)ethanone and 70.0 g (506 mmol) potassium carbonate. After dropwise addition, the reaction mixture was stirred at room temperature overnight, followed by heating to reflux temperature and continued stirring for 6 hours. Upon completion of the reaction, the reaction mixture was filtered while hot and the filtrate was concentrated to about 400 mL. ice water was added to the concentrate and a precipitate was precipitated. The precipitate was collected by filtration, dried and purified by chromatography using a short silica gel column (eluent ratio of dichloromethane:methanol = 99:1). The fractions containing the target product were combined, the solvent was evaporated and the residue was suspended in a mixed solvent of isopropanol/diisopropyl ether, diafiltered and washed with diisopropyl ether to give the pure product. Yield: 34.6 g (50% yield); MS data: [M + H]+ = 298. | | References | [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 4, p. 1410 - 1414
[2] Patent: US2005/267106, 2005, A1. Location in patent: Page/Page column 7
[3] Patent: WO2005/111005, 2005, A1. Location in patent: Page/Page column 16
[4] Patent: US2007/249595, 2007, A1. Location in patent: Page/Page column 11
[5] Patent: US2007/88160, 2007, A1. Location in patent: Page/Page column 11 |
| | 8-acetyl-6-(benzyloxy)-2H-benzo[b][1,4]oxazin-3(4H)-one Preparation Products And Raw materials |
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