Diethyl Ether → 8-Oxo-2,2,5,7-tetramethyl-7-(1-o-nitrobenzylcarbonyldioxymethyl)-3-oxa-1-azabicyclo[4.2.0]octane
反応式
[O:1]=[C:2]1[N:9]2[CH:4]([CH:5]([CH3:12])[CH2:6][O:7][C:8]2([CH3:11])[CH3:10])[C:3]1([CH3:15])[CH2:13][OH:14].[OH-:16].[K+].ClC(O[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[N+:29]([O-:31])=[O:30])=O.CC[O:34][CH2:35]C>>[O:1]=[C:2]1[N:9]2[CH:4]([CH:5]([CH3:12])[CH2:6][O:7][C:8]2([CH3:10])[CH3:11])[C:3]1([CH3:15])[CH2:13][O:14][O:16][C:35]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[N+:29]([O-:31])=[O:30])=[O:34]参加物
実験手順
Under anhydrous conditions at 0° C. a solution of 8-oxo-2,2,5,7-tetramethyl-7-(hydroxymethyl)-3-oxa-1-azabicyclo[4.2.0]octane (60 mg) in 0.6 ml ether is treated with powdered potassium hydroxide (19 mg). After a period of 15 minutes, o-nitrobenzyl chloroformate (65 mg) is added to the reaction mixture. Stirring is continued at 25° C. for an additional 15 hours. The mixture is partitioned between 1 M pH 7 phosphate buffer and more ether. The ether phase is washed with water and brine, dried over magnesium sulfate and filtered. Evaporation of the filtrate under reduced pressure gives a colorless oil. Purification by preparation thick-layer chromatography on silica gel developing with 1:9 ethylacetate/benzene gives 8-oxo-2,2,5,7-tetramethyl-7-(o-nitrobenzylcarbonyldioxymethyl)-3-oxa-1-azabicyclo-[4.2.0]octane as a mixture of diastereomers.
後処理
- waitis continued at 25° C. for an additional 15 hours
- customThe mixture is partitioned between 1 M pH 7 phosphate buffer and more ether
- washThe ether phase is washed with water and brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customEvaporation of the filtrate under reduced pressure
- customgives a colorless oil
- customPurification
- customby preparation thick-layer chromatography on silica gel developing with 1:9 ethylacetate/benzene
出典と根拠
- ORDレコード
- ord-8f23e66e81c04de2b3a31e9e06d81bde
- 出典データセット
- uspto-grants-1980_06
- 特許番号
- US04206219
反応ノート
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