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Sodium hydride → Diethyl {2-[4-({[2-[(tert-butoxycarbonyl)amino]-5-(2-thienyl)phenyl]amino}carbonyl)phenyl]-1-cyanoethyl}phosphonate

HRID 1013467
ノート
印刷プレビュー

反応式

HRID 1013467 の反応式
[C:1]([CH2:3][P:4](=[O:11])([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7])#[N:2].[H-].[Na+].Br[CH2:15][C:16]1[CH:43]=[CH:42][C:19]([C:20]([NH:22][C:23]2[CH:28]=[C:27]([C:29]3[S:30][CH:31]=[CH:32][CH:33]=3)[CH:26]=[CH:25][C:24]=2[NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:21])=[CH:18][CH:17]=1>C1COCC1.C(OCC)(=O)C>[C:37]([O:36][C:35]([NH:34][C:24]1[CH:25]=[CH:26][C:27]([C:29]2[S:30][CH:31]=[CH:32][CH:33]=2)=[CH:28][C:23]=1[NH:22][C:20]([C:19]1[CH:42]=[CH:43][C:16]([CH2:15][CH:3]([P:4](=[O:11])([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7])[C:1]#[N:2])=[CH:17][CH:18]=1)=[O:21])=[O:41])([CH3:40])([CH3:39])[CH3:38]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 57925962Tert-butyl [2-{[4-(bromomethyl)benzoyl]amino}-4-(2-thienyl)phenyl]carbamate

生成物 1

HCID 57925835Diethyl {2-[4-({[2-[(tert-butoxycarbonyl)amino]-5-(2-thienyl)phenyl]amino}carbonyl)phenyl]-1-cyanoethyl}phosphonate

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran
溶媒
2 回
HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

Diethyl cyanomethylphosphonate (0.19 ml, 1.175 mmol) was dissolved in THF (7 ml). The solution was cooled to 0° C. Sodium hydride (0.0818 g, 2.045 mmol) was added to the reaction. The reaction was allowed to stir for several minutes. Tert-butyl [2-{[4-(bromomethyl)benzoyl]amino}-4-(2-thienyl)phenyl]carbamate (0.5047 g, 1.035 mmol) was added in a solution of THF. The reaction was allowed to slowly warm to room temperature and stir overnight. The reaction was diluted with ethyl acetate and quenched with saturated aqueous ammonium chloride. The aqueous layer was extracted with ethyl acetate three times. The combined organic layer was dried over sodium sulfate, filtered, and concentrated. The resulting residue was partially purified by column chromatography on silica gel. MS: cal'd 484 (MH+-Boc), exp 484 (MH+-Boc).

後処理

  1. temperatureto slowly warm to room temperature
  2. stirringstir overnight
  3. customquenched with saturated aqueous ammonium chloride
  4. extractionThe aqueous layer was extracted with ethyl acetate three times
  5. dry with materialThe combined organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was partially purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-110ee8e2c6ce496f9a8df98e24943375
出典データセット
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07981874B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート