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Triacetoxyperiodinane → Morpholine-4-carboxylic acid [(S)-3,3-difluoro-1-((S)-1-formyl-1-methyl-butylcarbamoyl)-4-phenyl-butyl]-amide

HRID 1455604
ノート
印刷プレビュー

反応式

HRID 1455604 の反応式
[F:1][C:2]([F:31])([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:3][C@H:4]([NH:15][C:16]([N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)=[O:17])[C:5](=[O:14])[NH:6][C@@:7]([CH2:12][OH:13])([CH3:11])[CH2:8][CH2:9][CH3:10].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[F:31][C:2]([F:1])([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:3][C@H:4]([NH:15][C:16]([N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)=[O:17])[C:5](=[O:14])[NH:6][C@@:7]([CH:12]=[O:13])([CH3:11])[CH2:8][CH2:9][CH3:10]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 86607350morpholine-4-carboxylic acid [(S)-3,3-difluoro-1-((S)-1-hydroxymethyl-1-methyl-butylcarbamoyl)-4-phenyl-butyl]-amide

生成物 1

HCID 11305219Morpholine-4-carboxylic acid [(S)-3,3-difluoro-1-((S)-1-formyl-1-methyl-butylcarbamoyl)-4-phenyl-butyl]-amide収率 38.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of Morpholine-4-carboxylic acid [(S)-3,3-difluoro-1-((S)-1-hydroxymethyl-1-methyl-butylcarbamoyl)-4-phenyl-butyl]-amide (217 mg) and Dess-Martin Periodinane (15% in DCM, 2 eq.) in DCM (5 mL) is stirred at room temperature for 3 hrs and quenched with a solution of sodium thiosulfate in saturated NaHCO3. The product is extracted with ethyl acetate and washed with saturated NaCl solution. Organic phase is dried over anhydrous MgSO4, solvent evaporated under reduced pressure. Purification by silica gel chromatography eluting with ethyl acetate-heptane mixture gives Morpholine-4-carboxylic acid [(S)-3,3-difluoro-1-((S)-1-formyl-1-methyl-butylcarbamoyl)-4-phenyl-butyl]-amide (83 mg, 38%).

後処理

  1. customquenched with a solution of sodium thiosulfate in saturated NaHCO3
  2. extractionThe product is extracted with ethyl acetate
  3. washwashed with saturated NaCl solution
  4. dry with materialOrganic phase is dried over anhydrous MgSO4, solvent
  5. customevaporated under reduced pressure
  6. customPurification by silica gel chromatography
  7. washeluting with ethyl acetate-heptane mixture

出典と根拠

ORDレコード
ord-46c575c4720e4c11907de4bcbb5e0a1d
出典データセット
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07482448B2

反応ノート

読み込み中…

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