Carbon Dioxide → Methyl mandelate carbonate

HRID 992801노트

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HRID 992801 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 70167627Methyl mandelate carbonate수율 92%

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0f439d49b6e843abb243b44e15c123d6
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06469193B1

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