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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 1693409
ノート
印刷プレビュー

反応式

HRID 1693409 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-1dfe75d1a45d4b55be03eece2c134d42
出典データセット
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08158622B2

反応ノート

読み込み中…

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