Carbon Dioxide → Benzyl 3-phenylpropionate Carbonate

HRID 992802Notes

Reaction equation

HRID 992802 reaction equation
O[C@@H:2]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].[C:20](=[O:23])([O-:22])[O-:21].[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.O>[C:20](=[O:21])([OH:23])[OH:22].[C:14]1([CH2:13][CH2:2][C:3]([O:5][CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4])[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

8

Reactant 4

HCID 280Carbon Dioxide2×HCID 10796Cesium carbonateHCID 10377698Benzyl (S)-(-)-2-hydroxy-3-phenylpropionateHCID 16211592Merrifield's peptide resin

Product 1

HCID 70166888Benzyl 3-phenylpropionate CarbonateYield 73.3%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(S)-Benzyl 2-hydroxy-3-phenylpropionate (1.54 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 to solution. Carbon dioxide gas continuously bubbles 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, 1.33 g of resin is obtained (63% yield): IR3071, 3035, 2921, 2846, 1943, 1874, 1611, 1495, 1462, 1394, 1253, 1172, 1036, 765, 700 cm−1.

Workup

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

Sources & evidence

ORD record
ord-da6354325f2b48ca92d07f02a51d665c
Source dataset
uspto-grants-2002_10
Patent number
US06469193B1

Reaction notes

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