Sodium Bicarbonate → (3aR,4R,5R,6aS)-5-Benzyloxy-1-benzyloxycarbonyl-4-hydroxy-hexahydro-cyclopenta[c]isoxazole

HRID 1868171ノート

反応式

HRID 1868171 の反応式
C([O:9][C@@H:10]1[C@H:17]2[C@H:13]([NH:14][O:15][CH2:16]2)[CH2:12][C@H:11]1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=O)C1C=CC=CC=1.[C:26]([O:34][C@@H:35]1[C@@H]2[C@@H](NOC2)C[C@H]1OCC1C=CC=CC=1)(=O)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C[O-].[Na+].C(=O)([O-])[OH:55].[Na+].ClC(OOCC1C=CC=CC=1)=O>CO>[CH2:19]([O:18][C@@H:11]1[CH2:12][C@@H:13]2[N:14]([C:35]([O:34][CH2:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[O:55])[O:15][CH2:16][C@@H:17]2[C@H:10]1[OH:9])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

参加物

6

反応物 4

HCID 516892Sodium BicarbonateHCID 10942334Sodium MethoxideHCID 21874344HCID 21874344、化合物HCID 86602928(3aR,4R,5R,6aS)-4-Benzoyloxy-5-benzyloxy-hexahydro-cyclopenta[c]isoxazole (3aS,4R,5R,6aR)-4-benzoyloxy-5-benzyloxy-hexahydro-cyclopenta[c]isoxazole

生成物 1

HCID 67157658(3aR,4R,5R,6aS)-5-Benzyloxy-1-benzyloxycarbonyl-4-hydroxy-hexahydro-cyclopenta[c]isoxazole収率 18%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

The compound (4.08 g, 12.0 mmol) synthesized in Example 6 (6 g) was dissolved in methanol (40 mL) and sodium methoxide (696 μL, 3.61 mmol) was added thereto, followed by stirring of the mixture at room temperature for 2 hours. After Dowex 50W×8 was added thereto until the reaction mixture became neutral and it was filtered, the solvent was distilled off under reduced pressure. The residue was dissolved in ethyl acetate (40 mL) and saturated aqueous sodium hydrogencarbonate solution (20 mL) and benzyloxy chloroformate (2.4 mL, 16.8 mmol) were added thereto under ice-cooling, followed by stirring of the mixture at the same temperature for 1 hour and 30 minutes. The organic layer was washed with saturated brine (50 mL) and dried with anhydrous sodium sulfate, followed by distilling off of the solvent under reduced pressure. The residue was purified using silica gel flash column chromatography (hexane:ethyl acetate, 2:1-1:1, V/V) to obtain the desired title compound (789 mg, yield 18%) as a pale yellow solid and its diastereomer (1.62 g, yield 36%) as a pale yellow oil.

後処理

  1. filtrationit was filtered
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate (40 mL)
  4. temperatureunder ice-cooling
  5. stirringby stirring of the mixture at the same temperature for 1 hour and 30 minutes
  6. washThe organic layer was washed with saturated brine (50 mL)
  7. dry with materialdried with anhydrous sodium sulfate
  8. distillationby distilling off of the solvent under reduced pressure
  9. customThe residue was purified

出典と根拠

ORDレコード
ord-09713cf3f14e497ca3924fe07e6ed20d
出典データセット
uspto-grants-2009_12
特許番号
US07632930B2

反応ノート

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