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Dimethylformamide → HCID 178495951、化合物

HRID 926033
ノート
印刷プレビュー

反応式

HRID 926033 の反応式
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][S:12]([C:15]2[CH:16]=[C:17]([CH:27]=[CH:28][CH:29]=2)[C:18](OCC[Si](C)(C)C)=[O:19])(=[O:14])=[O:13])[CH2:7][CH2:6]1)=[O:4].CN(C=[O:34])C.Br[CH2:36][CH2:37][O:38][CH3:39].C(=O)([O-])[O-].[K+].[K+]>O>[CH3:1][O:2][C:3]([C@H:5]1[CH2:6][CH2:7][C@H:8]([N:11]([CH2:36][CH2:37][O:38][CH3:39])[S:12]([C:15]2[CH:16]=[C:17]([CH:27]=[CH:28][CH:29]=2)[C:18]([OH:19])=[O:34])(=[O:13])=[O:14])[CH2:9][CH2:10]1)=[O:4]
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 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 178501248HCID 178501248、化合物

生成物 1

HCID 178495951HCID 178495951、化合物

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

To a mixture of 1.00 g of 2-(trimethylsilyl)ethyl 3-{[trans-4-(methoxycarbonyl)cyclohexyl]sulfamoyl}benzoate and 10 mL of DMF were added 0.63 g of 2-bromoethylmethyl ether and 0.94 g of potassium carbonate at room temperature, followed by stirring at 60° C. overnight. The reaction mixture was cooled to room temperature, and then water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine in this order, and dried over anhydrous sodium sulfate. The resultant was concentrated under reduced pressure, and to a mixture of the obtained residue and 10 mL of THF was added a solution of TBAF in THF (1.0 M, 4.0 mL), followed by stirring at room temperature for 3 hours. A solution of TBAF in THF (1.0 M, 2.0 mL) was further added thereto, followed by stirring at room temperature for 1.5 hours. The reaction mixture was diluted with ethyl acetate, and then washed with 0.2 M hydrochloric acid, water, and saturated brine in this order. The obtained organic layer was dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain 915 mg of 3-{[trans-4-(methoxycarbonyl)cyclohexyl](2-methoxyethyl)sulfamoyl}benzoic acid as a colorless amorphous solid.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine in this order
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe resultant was concentrated under reduced pressure
  6. additionto a mixture of the obtained residue and 10 mL of THF
  7. additionwas added a solution of TBAF in THF (1.0 M, 4.0 mL)
  8. stirringby stirring at room temperature for 3 hours
  9. additionA solution of TBAF in THF (1.0 M, 2.0 mL) was further added
  10. stirringby stirring at room temperature for 1.5 hours
  11. additionThe reaction mixture was diluted with ethyl acetate
  12. washwashed with 0.2 M hydrochloric acid, water, and saturated brine in this order
  13. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  14. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-9415bec7f1bd4c5192f0258b8ed08506
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09284295B2

反応ノート

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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