Carbon Dioxide → Methyl mandelate carbonate

HRID 992801ノート

反応式

HRID 992801 の反応式
[C:1]([O:11][CH3:12])(=[O:10])[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].[C:13](=[O:16])([O-:15])[O-:14].[Cs+].[Cs+].C(=O)=O.C=CC1C=CC=CC=1.C=CC1C=CC(C=C)=CC=1.C1C=CC(CCl)=CC=1>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:13](=[O:14])([OH:16])[OH:15].[C:1]([O:11][CH3:12])(=[O:10])[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3]

参加物

7

反応物 4

HCID 280Carbon DioxideHCID 10796Cesium carbonateHCID 78066(+-)-Methyl mandelateHCID 16211592Merrifield's peptide resin

生成物 1

HCID 70167627Methyl mandelate carbonate収率 92%

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 6228Dimethylformamide溶媒

実験手順

Methyl mandelate(1 g, 6 mmol, 3 eq) is dissolved in anhydrous N,N-dimethylforamide (20 mL) to make a clear solution. Into the solution, are consecutively added cesium carbonate (1.95 g, 6 mmol) and tetrabutylammonium iodide (2.22 g, 6 mmol, 3 eq). The suspension is stirred at room temperature while passing carbon dioxide gas through for 1 hour before Merrifield's peptide resin (1 g, 2 mmol) is added to the solution. Carbon dioxide gas continuously bubbled through the solution and the reaction is allowed to proceed overnight at 60° C. The mixture is then cooled to room temperature, and diluted with water. The resin is washed successively with MeOH/H2O,H2O, 0.2 N HCl, H2O, THF, CH2Cl2, and MeOH. After drying under vacuum, 1.26 g of resin is obtained (76% yield): IR 3020, 2918, 2843, 1964, 1740, 1605, 1498, 1445, 1375, 1351, 1031, 771, 701, 551 cm−1.

後処理

  1. customthrough for 1 hour
  2. additionis added to the solution
  3. customCarbon dioxide gas continuously bubbled through the solution
  4. temperatureThe mixture is then cooled to room temperature
  5. additiondiluted with water
  6. washThe resin is washed successively with MeOH/H2O,H2O, 0.2 N HCl, H2O, THF, CH2Cl2, and MeOH
  7. customAfter drying under vacuum

出典と根拠

ORDレコード
ord-0f439d49b6e843abb243b44e15c123d6
出典データセット
uspto-grants-2002_10
特許番号
US06469193B1

反応ノート

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