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4-Methylmorpholine → Methyl 3-(4-chlorophenyl)-3-(4-(methylsulfonamido)-1H-indol-1-yl)pentanoate

HRID 1477916
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HRID 1477916 반응식
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[C:11]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)([CH2:17][CH3:18])[CH2:12][C:13]([O:15][CH3:16])=[O:14].CN1CCOCC1.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>C(Cl)Cl>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([C:11]([N:6]2[C:7]3[C:3](=[C:2]([NH:1][S:34]([CH3:33])(=[O:36])=[O:35])[CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:5]2)([CH2:17][CH3:18])[CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:20][CH:21]=1
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참가 물질

5

반응물 3

HCID 79724-MethylmorpholineHCID 31297Methanesulfonyl chlorideHCID 68175795Methyl 3-(4-amino-1H-indol-1-yl)-3-(4-chlorophenyl)pentanoate

생성물 1

HCID 70564698Methyl 3-(4-chlorophenyl)-3-(4-(methylsulfonamido)-1H-indol-1-yl)pentanoate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a mixture of the product of Step G (75 mg, 0.21 mmol) and NMM (42 mg, 0.42 mmol) in DCM (3 mL) was added methanesulfonyl chloride (36 mg, 0.38 mmol). Then the mixture was stirred at room temperature for 3 h, quenched with saturated ammonium chloride solution, and extracted with ethyl acetate. The organic layers were washed with brine (10 mL), dried over sodium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography (PE/EA=3/1) to afford the title compound as colorless oil. LC/MS m/z=435.1[M+H]+.

후처리

  1. customquenched with saturated ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. washThe organic layers were washed with brine (10 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by silica gel chromatography (PE/EA=3/1)

출처 및 근거

ORD 기록
ord-825dc7d2089b4917b702e67ca93a4543
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09403807B2

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