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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
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HRID 1455604 반응식
[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]
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참가 물질

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반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-46c575c4720e4c11907de4bcbb5e0a1d
출처 데이터셋
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07482448B2

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