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

HRID 2238329ノート

反応式

HRID 2238329 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-2a2d6e44d9ed435ea8d5e181f4cfbbfa
出典データセット
uspto-grants-2010_05
特許番号
US07718633B2

反応ノート

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