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Acetonitrile → HCID 57524147, 화합물

HRID 1427249
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HRID 1427249 반응식
[C:1](#[N:3])[CH3:2].[Li]CCCC.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([N:23]2[C:31]3[C:26](=[C:27]([NH:32][S:33]([CH3:36])(=[O:35])=[O:34])[CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24]2)([CH2:21][CH3:22])[C:17](OC)=[O:18])=[CH:12][CH:11]=1>O1CCCC1>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([N:23]2[C:31]3[C:26](=[C:27]([NH:32][S:33]([CH3:36])(=[O:34])=[O:35])[CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24]2)([CH2:21][CH3:22])[C:17](=[O:18])[CH2:2][C:1]#[N:3])=[CH:12][CH:11]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 6342AcetonitrileHCID 57524786HCID 57524786, 화합물HCID 178418339Butyllithium

생성물 1

HCID 57524147HCID 57524147, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of acetonitrile (180 mg, 4.4 mmol) in tetrahydrofuran (3 mL) was added BuLi (1.9 mL, 4.8 mmol, 2.5 M in hexane) at −78° C. After stirring for 30 min, a solution of methyl 2-(4-chlorophenyl)-2-(4-(methylsulfonamido)-1H-indol-1-yl)butanoate (840 mg, 2.0 mmol, Enantiomer A), as described in Example 3 step D, in tetrahydrofuran (3 mL) was added to the mixture at −78° C. The resulting mixture was stirred at −78° C. for another 1 h, and then quenched with water (15 mL), extracted with ethyl acetate. The combined organics were washed with brine (15 mL), dried over Na2SO4, filtered and concentrated. The crude product was purified by silica gel chromatography eluting with PE/EA (5/1 to 3/1, v/v) to get the title compound as a colorless amorphous solid (Enantiomer A). LC/MS m/z=429.8[M+H]+.

후처리

  1. additionwas added to the mixture at −78° C
  2. stirringThe resulting mixture was stirred at −78° C. for another 1 h
  3. customquenched with water (15 mL)
  4. extractionextracted with ethyl acetate
  5. washThe combined organics were washed with brine (15 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by silica gel chromatography
  10. washeluting with PE/EA (5/1 to 3/1

출처 및 근거

ORD 기록
ord-c073bac6dd524f479de2bc71fcc9bb7d
출처 데이터셋
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08933113B2

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