Carbon Dioxide → Methyl mandelate carbonate

HRID 992801Notes

Reaction equation

HRID 992801 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

HCID 70167627Methyl mandelate carbonateYield 92%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0f439d49b6e843abb243b44e15c123d6
Source dataset
uspto-grants-2002_10
Patent number
US06469193B1

Reaction notes

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