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Triphenylphosphine → 3-(4-(4-(6-Cyano-3-pyridazinyl)piperazin-1-yl)-3-fluorophenyl)-5(R)-(isoxazol-3-yl)oxymethyloxazolidin-2-one

HRID 1167484
ノート
印刷プレビュー

反応式

HRID 1167484 の反応式
[C:1]([C:3]1[N:8]=[N:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:25][C@H:24]([CH2:26][OH:27])[O:23][C:22]4=[O:28])=[CH:17][C:16]=3[F:29])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2].O[C:31]1[CH:35]=[CH:34][O:33][N:32]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>>[C:1]([C:3]1[N:8]=[N:7][C:6]([N:9]2[CH2:10][CH2:11][N:12]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:25][C@H:24]([CH2:26][O:27][C:31]5[CH:35]=[CH:34][O:33][N:32]=5)[O:23][C:22]4=[O:28])=[CH:17][C:16]=3[F:29])[CH2:13][CH2:14]2)=[CH:5][CH:4]=1)#[N:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 213566023-(4-(4-(6-Cyano-3-pyridazinyl)piperazin-1-yl)-3-fluorophenyl)-5(R)-hydroxy methyloxazolidin-2-oneHCID 178516613HCID 178516613、化合物

生成物 1

HCID 699799723-(4-(4-(6-Cyano-3-pyridazinyl)piperazin-1-yl)-3-fluorophenyl)-5(R)-(isoxazol-3-yl)oxymethyloxazolidin-2-one収率 25.8%

実験手順

3-(4-(4-(6-Cyano-3-pyridazinyl)piperazin-1-yl)-3-fluorophenyl)-5(R)-hydroxy methyloxazolidin-2-one (398 mg, 1 mmol), 3-hydroxyisoxazole (93.5 mg, 1.1 mmol) and triphenylphosphine (328 mg, 1.25 mmol), were suspended with stirring in dry tetrahydrofiran (10 ml). Diisopropylazodicarboxylate (242 mg, 1.2 mmol) was added dropwise by syringe, and the mixture stirred at ambient temperature for 30 minutes. The reaction mixture was filtered, evaporated to dryness, dissolved in EtOAc/isohexane (1:1), and applied to a 10 g silica Mega Bond Elut® column, eluting with a gradient from 75 to 100% EtOAc in isohexane. Relevant fractions were combined and evaporated to give the title compound (120 mg).

後処理

  1. stirringthe mixture stirred at ambient temperature for 30 minutes
  2. filtrationThe reaction mixture was filtered
  3. customevaporated to dryness
  4. dissolutiondissolved in EtOAc/isohexane (1:1)
  5. washeluting with a gradient from 75 to 100% EtOAc in isohexane
  6. customevaporated

出典と根拠

ORDレコード
ord-4ab8488b229d4b51af22bd24167211a5
出典データセット
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06617339B1

反応ノート

読み込み中…

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