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Piconol → N-{(2S)-5-[(2-pyridinylmethyl)oxy]-2,3-dihydro-1H-inden-2-yl}-2-propanesulfonamide

HRID 1922299
ノート
印刷プレビュー

反応式

HRID 1922299 の反応式
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C@H:6]([NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH2:5]2.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>ClCCl>[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C@H:6]([NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH2:5]2
参加物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 11474PiconolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 66857149(S)-N-(5-hydroxy-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide

生成物 1

HCID 44124831N-{(2S)-5-[(2-pyridinylmethyl)oxy]-2,3-dihydro-1H-inden-2-yl}-2-propanesulfonamide収率 51.8%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

A solution of N-[(2S)-5-hydroxy-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide (100 mg, 0.39 mmol, Description 3) and 2-pyridinylmethanol (43 mg, 0.39 mmol) in dichloromethane (3 ml), was treated with triphenylphosphine (103 mg, 0.39 mmol) and then diisopropyl azodicarboxylate (77 ul, 0.39 mmol). The resulting solution was stirred at room temperature, under an atmosphere of argon, for 16 hours. The solution was then partitioned between water and dichloromethane and the organic solution was dried (MgSO4) and evaporated under reduced pressure to yield the crude product. The crude product was purified using MDAP. The resulting solution was diluted with saturated aqueous sodium bicarbonate solution and extracted with dichloromethane. The organic solution was dried (MgSO4) and evaporated under reduced pressure to obtain the title compound as a white solid (70 mg).

後処理

  1. customThe solution was then partitioned between water and dichloromethane
  2. dry with materialthe organic solution was dried (MgSO4)
  3. customevaporated under reduced pressure
  4. customto yield the crude product
  5. customThe crude product was purified
  6. additionThe resulting solution was diluted with saturated aqueous sodium bicarbonate solution
  7. extractionextracted with dichloromethane
  8. dry with materialThe organic solution was dried (MgSO4)
  9. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-5706f29940e842ca90caf26f021259fd
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08173820B2

反応ノート

読み込み中…

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