Water → (R)-1,1-dibenzyl 2-ethyl propane-1,1,2-tricarboxylate

HRID 1487180Notes

Reaction equation

HRID 1487180 reaction equation
CS(O[C@H:6]([CH3:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=O)=O.[C:13]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=[O:25])[CH2:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16].[F-].[Cs+].O>CN(C=O)C>[CH:14]([C:13]([O:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:25])([C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[C@H:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 25953Cesium fluorideHCID 84754Dibenzyl malonateHCID 2723759Propanoic acid, 2-[(methylsulfonyl)oxy]-, ethyl ester, (R)-

Product 1

HCID 86699677(R)-1,1-dibenzyl 2-ethyl propane-1,1,2-tricarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (R)-ethyl 2-(methylsulfonyloxy)propanoate (15 g, 0.076 mol) in DMF (300 ml) was added dibenzyl malonate (21.5 g, 0.076 mol) and CsF (11.5 g, 0.076 mol). The mixture was heated to 50° C. for 2 days. After cooled to room temperature, the mixture was poured into water and then extracted with EtOAc. The organic phase was washed with brine, water and dried. Concentrated to afford (R)-1,1-dibenzyl 2-ethyl propane-1,1,2-tricarboxylate, which was purified by silica gel chromatography (11 g, 40%).

Workup

  1. temperatureAfter cooled to room temperature
  2. extractionextracted with EtOAc
  3. washThe organic phase was washed with brine, water
  4. customdried
  5. concentrationConcentrated

Sources & evidence

ORD record
ord-bba6c303198442ecaa2fde33d15cd605
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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