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Sodium Sulfite → 5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [1-(S)-(tert-butyldimethylsilanyloxymethyl)-2-oxo-2-phenylethyl]amide

HRID 751664
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HRID 751664 반응식
[Si:1]([O:8][CH2:9][C@H:10]([NH:19][C:20]([C:22]1[NH:31][C:25]2=[CH:26][N:27]=[C:28]([Cl:30])[CH:29]=[C:24]2[CH:23]=1)=[O:21])[C@@H:11]([OH:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].[O-]S([O-])=O.[Na+].[Na+]>C(Cl)Cl.C([O-])(O)=O.[Na+].C(OCC)(=O)C>[Si:1]([O:8][CH2:9][C@H:10]([NH:19][C:20]([C:22]1[NH:31][C:25]2=[CH:26][N:27]=[C:28]([Cl:30])[CH:29]=[C:24]2[CH:23]=1)=[O:21])[C:11](=[O:18])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]
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참가 물질

8

반응물 4

HCID 24437Sodium SulfiteHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 575501065-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [1-(S)-(tert-butyldimethylsilanyloxymethyl)-2-(S)-hydroxy-2-phenylethyl]amide

생성물 1

HCID 597535505-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [1-(S)-(tert-butyldimethylsilanyloxymethyl)-2-oxo-2-phenylethyl]amide

시약·촉매·용매 3

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매HCID 516892Sodium Bicarbonate용매

실험 절차

To a solution of 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [1-(S)-(tert-butyldimethylsilanyloxymethyl)-2-(S)-hydroxy-2-phenylethyl]amide (Preparation 100, 304 mg, 0.661 mmol) in dry DCM (10 mL) was added Dess-Martin periodinane (342 mg, 0.806 mmol). After stirring for 3 h at room temperature alkaline sodium thiosulfate solution was added (5.4 g Na2SO3 dissolved in 20 mL saturated NaHCO3 solution) and the emulsion vigorously stirred for an additional 30 min. Ethyl acetate (150 ml) was added and the aqueous layer removed. The organic layer was washed with brine (50 ml), dried (MgSO4) and concentrated to a residue which was purified by flash chromatography on silica gel (eluent: hexane/ethyl acetate:50/50) to give the title compound as colourless solid. m/z (ES+)=458.34 [M+H]+; RT=4.32 min.

후처리

  1. additionwas added
  2. customthe aqueous layer removed
  3. washThe organic layer was washed with brine (50 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated to a residue which
  6. customwas purified by flash chromatography on silica gel (eluent: hexane/ethyl acetate:50/50)

출처 및 근거

ORD 기록
ord-35e488e11fad489daa54b6376763ef9e
출처 데이터셋
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07405210B2

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