(+-)-3-Phenyllactic acid → HCID 4292412, compound

HRID 732859Notes

Reaction equation

HRID 732859 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH:8]([OH:12])[C:9]([OH:11])=[O:10])=[CH:3][CH:2]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C.CCOC(C)=O>[CH2:19]([O:10][C:9](=[O:11])[CH:8]([OH:12])[CH2:7][C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 3848(+-)-3-Phenyllactic acidHCID 7498Benzyl BromideHCID 10796Cesium carbonate

Product 1

HCID 4292412HCID 4292412, compoundYield 93.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of DL-Phenyllactic acid (5.0 g, 30.09 mmol) in DMF (30 mL) was added Cs2CO3 (10.79 g, 33.11 mmol) in portions during 10 minutes period at room temperature. The resulting mixture was stirred for 15 min at room temperature, followed by the addition of benzyl bromide (3.57 mL, 30.09 mmol). The resulting mixture was stirred at room temperature overnight. The reaction mixture was diluted with EtOAc (300 mL), washed with saturated NaHCO3, water (100×2) and brine, dried (Na2SO4) and filtered. The filtrate was concentrated to give 7.20 g (89%) of the title compound.

Workup

  1. stirringThe resulting mixture was stirred at room temperature overnight
  2. washwashed with saturated NaHCO3, water (100×2) and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-c90f5ecad0e44e6b8f16ab6123e32b3c
Source dataset
uspto-grants-2009_09
Patent number
US07589067B2

Reaction notes

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