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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
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HRID 1167484 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 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, 화합물

생성물 1

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

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4ab8488b229d4b51af22bd24167211a5
출처 데이터셋
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06617339B1

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