Citric Acid → 4-[(Di-tert-butoxyphosphoryl)oxy]-3,3-dimethylbutanoic acid

HRID 2238329노트

반응식

HRID 2238329 반응식
[P:1]([O:13][CH2:14][C:15]([CH3:20])([CH3:19])[CH2:16][CH2:17][OH:18])([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:22].[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>[C:9]([O:8][P:1]([O:13][CH2:14][C:15]([CH3:20])([CH3:19])[CH2:16][C:17]([OH:22])=[O:18])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])([CH3:10])([CH3:11])[CH3:12]

참가 물질

5

반응물 3

HCID 311Citric AcidHCID 2724130Cornforth reagentHCID 86616511Di-tert-butyl 4-hydroxy-2,2-dimethylbutyl phosphate

생성물 1

HCID 860938834-[(Di-tert-butoxyphosphoryl)oxy]-3,3-dimethylbutanoic acid수율 60%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of the product from Example 10C (0.235 g, 0.76 mmol) in DMF (7.6 mL) at room temperature was added pyridinium dichromate (1.71 g), and the mixture was stirred for 16 hours. 10% citric acid was added and the reaction mixture 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 starting with chloroform and ending with 5% methanol in chloroform, to give the title compound (0.144 g, 60%).

후처리

  1. extractionthe reaction mixture 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

출처 및 근거

ORD 기록
ord-2a2d6e44d9ed435ea8d5e181f4cfbbfa
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07718633B2

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