Potassium Hydroxide → (2R)-2-benzyl-3-ethoxy-2-hydroxy-3-oxopropanoic acid

HRID 717311Notes

Reaction equation

HRID 717311 reaction equation
[CH2:1]([C:8]([OH:19])([C:14]([O:16]CC)=[O:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>CCO>[CH2:1]([C@:8]([OH:19])([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:14]([OH:16])=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 15828909Ethyl 3-phenyl-2-hydroxy-2-ethoxycarbonyl-propanoate

Product 1

HCID 71727620(2R)-2-benzyl-3-ethoxy-2-hydroxy-3-oxopropanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To diethyl benzyl(hydroxy)propanedioate (6.3 g) in 50 mL of EtOH (anhydrous) was added KOH (1.5 g). The mixture was stirred at rt over night. After removing the solvent in vacuo, the residue was taken up with 100 mL of ethyl acetate and 150 mL of water. The organic layer was removed. To the aqueous layer containing the potassium salt of the desired product was added 0.2 N HCl until pH=2. The mixture was extracted with 200 mL ethyl acetate. The organic layer was dried with magnesium sulfate and concentrated to give the title acid as a colorless oil. The racemic acid was then purified by chrial SFC(OJ-H, 4.6×100 mm, 5% MeOH/0.1% TFA/CO2, 2.5 mL/min, 100 bar) to give the title compound as a single enantiomer. LC/MS 261.1 (M+23).

Workup

  1. customAfter removing the solvent in vacuo
  2. customThe organic layer was removed
  3. additionTo the aqueous layer containing the potassium salt of the desired product
  4. additionwas added 0.2 N HCl until pH=2
  5. extractionThe mixture was extracted with 200 mL ethyl acetate
  6. dry with materialThe organic layer was dried with magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-98852bd420c04964899cf99420ed0318
Source dataset
uspto-grants-2015_11
Patent number
US09193717B2

Reaction notes

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