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Citric Acid → 4-{[Bis(benzyloxy)phosphoryl]oxy}-3,3-dimethylbutanoic acid

HRID 1968911
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HRID 1968911 반응식
[P:1]([O:19][CH2:20][C:21]([CH3:26])([CH3:25])[CH2:22][CH2:23][OH:24])([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:28].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[CH2:4]([O:3][P:1]([O:19][CH2:20][C:21]([CH3:26])([CH3:25])[CH2:22][C:23]([OH:28])=[O:24])([O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:2])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1
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참가 물질

5

반응물 3

HCID 311Citric AcidHCID 2724130Cornforth reagentHCID 54009748Dibenzyl 4-hydroxy-2,2-dimethylbutyl phosphate

생성물 1

HCID 540936554-{[Bis(benzyloxy)phosphoryl]oxy}-3,3-dimethylbutanoic acid수율 85.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of the product from Example 9B (0.396 g, 1.0 mmol) in DMF (10 mL) at room temperature was added pyridinium dichromate (2.3 g), and the mixture was stirred for 48 hours. 10% citric acid was added and the reaction was extracted twice with ethyl acetate. The combined organic layer was washed with brine, dried over MgSO4, filtered and evaporated. The residue was purified by chromatography on silica gel, eluting with a gradient of 0-5% methanol in chloroform, to give the title compound (0.334 g, 81%).

후처리

  1. extractionthe reaction was extracted twice with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography on silica gel
  7. washeluting with a gradient of 0-5% methanol in chloroform

출처 및 근거

ORD 기록
ord-c49d69730f1c4e409055f192f5b34435
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08426388B2

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