Trifluoroacetic acid → 5-[([4H,5H,6H-cyclopenta[b]thiophen-2-yl]amino)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 2178984

反応式

HRID 2178984 の反応式
[S:1]1[C:5]([NH:6][C:7](=O)OC(C)(C)C)=[CH:4][C:3]2[CH2:14][CH2:15][CH2:16][C:2]1=2.FC(F)(F)C(O)=O.C(OC=[C:28]1[C:33](=[O:34])[O:32][C:31]([CH3:36])([CH3:35])[O:30][C:29]1=[O:37])C>C(Cl)Cl>[S:1]1[C:5]([NH:6][CH:7]=[C:28]2[C:33](=[O:34])[O:32][C:31]([CH3:36])([CH3:35])[O:30][C:29]2=[O:37])=[CH:4][C:3]2[CH2:14][CH2:15][CH2:16][C:2]1=2

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 53237235-(Ethoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dioneHCID 66545155Carbamic acid, N-(5,6-dihydro-4H-cyclopenta[b]thien-2-yl)-, 1,1-dimethylethyl ester

生成物 1

HCID 867080805-[([4H,5H,6H-cyclopenta[b]thiophen-2-yl]amino)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione収率 92%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of tert-butyl N-[4H,5H,6H-cyclopenta[b]thiophen-2-yl]carbamate (480 mg, 2.01 mmol, 1.00 equiv) in 15 mL of DCM was added trifluoroacetic acid (460 mg, 4.03 mmol, 2.00 equiv) at 0° C. After stirring at room temperature for 4 h, the resulting solution was concentrated under vacuum. The pH value was adjusted to 8 with saturated aqueous NaHCO3 solution and extracted with dichloromethane (60 mL×3). Then 5-(ethoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione [prepared by heating 2,2-dimethyl-1,3-dioxane-4,6-dione (580 mg, 4.02 mmol, 2.00 equiv) in 6.0 g of (diethoxymethoxy)ethane at 100° C. for 1 h followed by cooling to room temperature] was added to the above extracts. Drying over sodium sulfate followed by concentration in vacuo afforded 5-[([4H,5H,6H-cyclopenta[b]thiophen-2-yl]amino)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione (0.54 g, 92%) as a yellow solid which was used in the next step without further purification.

後処理

  1. concentrationthe resulting solution was concentrated under vacuum
  2. extractionextracted with dichloromethane (60 mL×3)
  3. dry with materialDrying over sodium sulfate
  4. concentrationfollowed by concentration in vacuo

出典と根拠

ORDレコード
ord-562ab8bf866540a89182c54c59f10c14
出典データセット
uspto-grants-2015_06
特許番号
US09067948B2

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