反応式
[NH2:1][C@@:2]12[CH2:7][C@H:6]1[CH2:5][O:4][C:3]2=[O:8].[F:9][C:10]([F:16])([F:15])[CH2:11][C:12](O)=[O:13].OC1C2N=NNC=2C=CC=1.C(N=C=NCCCN(C)C)C>CN(C)C=O.O.C(N(CC)CC)C>[F:9][C:10]([F:16])([F:15])[CH2:11][C:12]([NH:1][C@@:2]12[CH2:7][C@H:6]1[CH2:5][O:4][C:3]2=[O:8])=[O:13]参加物
反応物 4
生成物 1
試薬・触媒・溶媒 3
実験手順
(±)-Trans-1-amino-3-oxabicyclo[3.1.0]hexan-2-one (128 mg, 1.13 mmol) was mixed with 3,3,3-trifluoropropionic acid in 2.3 mL of N,N-dimethylformamide. Hydroxybenzotriazole (17.4 mg, 0.11 mmol) was added followed by 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (282 mg, 1.47 mmol). The pH of the reaction mixture was adjusted to 8.5 with triethylamine and the mixture was allowed to stir at ambient temperature for 2 hours. Water was then added and the reaction mixture was extracted with ethyl acetate. The combined organic extracts were washed with water and brine, then dried (sodium sulfate) and concentrated to give the crude product. This was purified by silica gel chromatography to afford 120 mg (45%) of 3,3,3-trifluoro-N-[(±)-trans-2-oxo-3-oxabicyclo[3.1.0]hex-1-yl]-propanamide.
後処理
- extractionthe reaction mixture was extracted with ethyl acetate
- washThe combined organic extracts were washed with water and brine
- dry with materialdried (sodium sulfate)
- concentrationconcentrated
- customto give the crude product
- customThis was purified by silica gel chromatography
出典と根拠
- ORDレコード
- ord-0300c97a88a5417abebd157852f56576
- 出典データセット
- uspto-grants-2006_08
- 特許番号
- US07091380B2
関連ノート
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