Dimethylformamide → HCID 68322429、化合物
反応式
[CH3:1][C:2]([O:5][C:6]([NH:8][C@@H:9]([C:11]([OH:13])=O)[CH3:10])=[O:7])([CH3:4])[CH3:3].CN(C)C=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:41][C:42]1[CH:47]=[CH:46][C:45]([O:48][C:49]2[CH:55]=[CH:54][C:52]([NH2:53])=[CH:51][CH:50]=2)=[CH:44][C:43]=1[O:56][CH3:57]>>[CH3:10][C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:2]([CH3:1])([CH3:3])[CH3:4])[C:11]([NH:53][C:52]1[CH:51]=[CH:50][C:49]([O:48][C:45]2[CH:46]=[CH:47][C:42]([CH3:41])=[C:43]([O:56][CH3:57])[CH:44]=2)=[CH:55][CH:54]=1)=[O:13]参加物
実験手順
To a solution of N-{[(1,1-dimethylethyl)oxy]carbonyl}-D-alanine (182 mg, 0.960 mmol) in dry N,N-Dimethylformamide (DMF) (4 mL) DIPEA (0.305 mL, 1.745 mmol) and then TBTU (336 mg, 1.047 mmol) were added and the reaction mixture was stirred for 15 minutes at r.t. 4-{[4-methyl-3-(methyloxy)phenyl]oxy}aniline (Intermediate 20, 200 mg) was then added and the reaction mixture was stirred for 1 hour at the same temperature. The reaction was quenched with water (2 mL), diluted with brine (10 mL) and extracted with ethyl acetate (2 times 20 mL). Organic layer was dried over sodium sulphate, filtered and evaporated and the residue was purified by flash chromatography (Biotage system, 10 g SNAP column) using as eluent a gradient cyclohexane/ethyl acetate from 100/0 to 80/20 to afford the title compound as a yellow pale solid (304 mg).
後処理
- stirringthe reaction mixture was stirred for 1 hour at the same temperature
- customThe reaction was quenched with water (2 mL)
- additiondiluted with brine (10 mL)
- extractionextracted with ethyl acetate (2 times 20 mL)
- dry with materialOrganic layer was dried over sodium sulphate
- filtrationfiltered
- customevaporated
- customthe residue was purified by flash chromatography (Biotage system, 10 g SNAP column)
出典と根拠
- ORDレコード
- ord-3bcea0eaf6d54d919071ffb8fc780287
- 出典データセット
- uspto-grants-2015_12
- 特許番号
- US09216967B2
反応ノート
読み込み中…