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Sodium Chlorite → 3-[4-(Benzenesulfonylmethyl)-3-tert-butoxycarbonyl-2-hydroxyphenyl]-furan-2-carboxylic acid

HRID 1778349
ノート
印刷プレビュー

反応式

HRID 1778349 の反応式
OP([O-])(O)=O.[Na+].[C:7]1([S:13]([CH2:16][C:17]2[C:22]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[C:21]([OH:30])[C:20]([C:31]3[CH:35]=[CH:34][O:33][C:32]=3[CH:36]=[O:37])=[CH:19][CH:18]=2)(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl([O-])=[O:39].[Na+]>O.C(#N)C.OO>[C:7]1([S:13]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([C:31]3[CH:35]=[CH:34][O:33][C:32]=3[C:36]([OH:39])=[O:37])=[C:21]([OH:30])[C:22]=2[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])(=[O:15])=[O:14])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 23668197Sodium Chlorite2 回HCID 23672064Monosodium phosphate2 回HCID 86684731Tert-butyl 6-(benzenesulfonylmethyl)-3-(2-formylfuran-3-yl)-2-hydroxybenzoate2 回

生成物 1

HCID 666926633-[4-(Benzenesulfonylmethyl)-3-tert-butoxycarbonyl-2-hydroxyphenyl]-furan-2-carboxylic acid収率 25.7%

試薬・触媒・溶媒 3

HCID 784
Hydrogen Peroxide
溶媒
2 回
HCID 962Water溶媒2 回
HCID 6342Acetonitrile溶媒

実験手順

A solution of sodium phosphate monobasic (0.039 g) in water (1 mL) was added to a solution of tert-butyl 6-(benzenesulfonylmethyl)-3-(2-formylfuran-3-yl)-2-hydroxybenzoate (Intermediate 27, 0.105 g) in acetonitrile (2 mL) at 0° C. Hydrogen peroxide (50% wt. in water, 0.078 mL) and sodium chlorite (0.029 g) were added and the reaction mixture was warmed to room temperature and stirred for 18 hours. The mixture was cooled to 0° C. and further sodium phosphate monobasic (0.028 g) in water (0.5 mL), hydrogen peroxide (50% wt. in water, 0.038 mL) and sodium chlorite (0.052 g) were added and the mixture was warmed to room temperature and stirred for 18 hours. The mixture was poured onto sodium sulfite (10% in water) at 0° C., extracted into ethyl acetate, washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of methanol and 1% acetic acid in methanol with a gradient of O-100%. The resultant product was triturated in cyclohexane and ethyl acetate and the solid was collected by filtration and dried in vacuo to give 3-[4-(benzenesulfonylmethyl)-3-tert-butoxycarbonyl-2-hydroxy-phenyl]-furan-2-carboxylic acid (0.028 g) as a white solid.

後処理

  1. temperatureThe mixture was cooled to 0° C.
  2. temperaturethe mixture was warmed to room temperature
  3. stirringstirred for 18 hours
  4. additionThe mixture was poured onto sodium sulfite (10% in water) at 0° C.
  5. extractionextracted into ethyl acetate
  6. washwashed with water
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customThe filtrate was evaporated to dryness
  10. customthe residue was purified by chromatography on silica
  11. washeluting with a mixture of methanol and 1% acetic acid in methanol with a gradient of O-100%
  12. customThe resultant product was triturated in cyclohexane
  13. filtrationethyl acetate and the solid was collected by filtration
  14. customdried in vacuo

出典と根拠

ORDレコード
ord-3a95b30ccf604127ad147b642f99b05a
出典データセット
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09266896B2

反応ノート

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