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P,P-Diphenylphosphinic azide → 3-[5-(1-Azido-ethyl)-4-methyl-thiophen-2-yl]-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole

HRID 2045952
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HRID 2045952 반응식
C1(P([N:15]=[N+:16]=[N-:17])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCC=C1CCCCN2.[Cl:29][C:30]1[CH:31]=[C:32]([C:37]2([C:51]([F:54])([F:53])[F:52])[O:41][N:40]=[C:39]([C:42]3[S:46][C:45]([CH:47](O)[CH3:48])=[C:44]([CH3:50])[CH:43]=3)[CH2:38]2)[CH:33]=[C:34]([Cl:36])[CH:35]=1>C1(C)C=CC=CC=1>[N:15]([CH:47]([C:45]1[S:46][C:42]([C:39]2[CH2:38][C:37]([C:32]3[CH:31]=[C:30]([Cl:29])[CH:35]=[C:34]([Cl:36])[CH:33]=3)([C:51]([F:54])([F:53])[F:52])[O:41][N:40]=2)=[CH:43][C:44]=1[CH3:50])[CH3:48])=[N+:16]=[N-:17]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 199401P,P-Diphenylphosphinic azideHCID 9834010Diazabicyclo[5.4.0]undec-7-eneHCID 665872011-{5-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophen-2-yl}-ethanol

생성물 1

HCID 866812913-[5-(1-Azido-ethyl)-4-methyl-thiophen-2-yl]-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole

시약·촉매·용매 1

HCID 1140
Toluene
용매

실험 절차

Diphenylphosphoryl azide (0.53 ml) and diazabicyclo-[5.4.0]-undec-7-ene (DBU, 0.40 ml) is added to a solution of 1-{5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophen-2-yl}-ethanol (0.87 g) in toluene (9 ml). After 19 hours at room temperature, the reaction is quenched with a saturated aqueous solution of NH4Cl in water. The reaction mixture is extracted three times with ethyl acetate. The organic phases are combined, dried over MgSO4 and concentrated in vacuo. The crude product is purified on a semi-preparative HPLC to yield 3-[5-(1-azido-ethyl)-4-methyl-thiophen-2-yl]-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole (0.64 g) as a yellow oil. MS (HPLC/MS): 449 (MH+). Retention time: 2.45 min.

후처리

  1. customthe reaction is quenched with a saturated aqueous solution of NH4Cl in water
  2. extractionThe reaction mixture is extracted three times with ethyl acetate
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product is purified on a semi-preparative HPLC

출처 및 근거

ORD 기록
ord-110771fc591b4c11be586642b342b5ab
출처 데이터셋
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08592418B2

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