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Lithium diisopropylamide → HCID 69253567, 화합물

HRID 902756
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HRID 902756 반응식
[CH3:1][O:2][C:3](=[O:42])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[C:32]=2[Cl:41])[CH2:16][CH:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=1.[CH:43]([N-]C(C)C)([CH3:45])[CH3:44].[Li+].IC(I)(C)C>C1COCC1>[CH3:1][O:2][C:3]([C:4]1([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:38])([F:39])[F:40])[C:32]=3[Cl:41])[CH2:16][CH:17]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:6]=2)[CH2:45][CH2:43][CH2:44]1)=[O:42]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 2724682Lithium diisopropylamideHCID 10188816Methyl (3-{3-[[2-Chloro-3-(trifluoromethyl)benzyl](2,2-diphenylethyl)amino]propoxy}-phenyl)acetateHCID 11483316Propane, 2,2-diiodo-

생성물 1

HCID 69253567HCID 69253567, 화합물수율 50%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

To a solution of (3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-acetic acid methyl ester (100 mg, 0.17 mmol) in dry THF (50 ml) was added lithium diisopropylamide (1.26 ml, 0.5 mmol) dropwise with cooling to −78° C. After the reaction mixture was stirred at −78° C. for an additional 1 h, diiodo-propane (152 mg, 0.51 mmol) was added. The reaction was warmed to room temperature over 4 h followed by quenching with saturated ammonium chloride (10 ml). Solvent was removed and the residue was partitioned between water and ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated under vacuum. The residue was purified by silica gel column chromatograph (EtOAc:Hexane/20:80) to give the title compound as an oil (40 mg, 50%). MS m/e 636.2 (M+H)+.

후처리

  1. temperatureThe reaction was warmed to room temperature over 4 h
  2. customby quenching with saturated ammonium chloride (10 ml)
  3. customSolvent was removed
  4. customthe residue was partitioned between water and ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by silica gel column chromatograph (EtOAc:Hexane/20:80)

출처 및 근거

ORD 기록
ord-188c931b03f745a5b9f1532c22186a9d
출처 데이터셋
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07365085B2

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