Formic Acid → (R)-3-phenyllactic acid

HRID 557482Notes

Reaction equation

HRID 557482 reaction equation
[C:1]1([CH2:7][C:8](=[O:12])[C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.C(O)=O>CC1C=CC(S(N[C@@H]([C@H](N)C2C=CC=CC=2)C2C=CC=CC=2)(=O)=O)=CC=1.C(N(CC)CC)C.CO>[OH:12][C@H:8]([CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:9]([OH:11])=[O:10]

Participants

7

Reactant 3

HCID 284Formic AcidHCID 997Phenylpyruvic acidHCID 8471Triethylamine

Product 1

HCID 643327(R)-3-phenyllactic acidYield 101.2%

Reagents, catalysts & solvents 3

HCID 8471TriethylamineCatalystHCID 2734565N-((1R,2R)-2-Amino-1,2-diphenylethyl)-4-methylbenzene-1-sulfonamideCatalystHCID 887MethanolSolvent2×

Procedure

Into 1 ml of methanol were dissolved 7 mg (0.01 mmol) of [RuCl2(p-cymene)]2 and 8 mg (0.02 mmol) of (R,R)-TsDPEN to prepare a solution, and to the solution was dropwise added 2 mg (0.02 mmol) of triethylamine, followed by stirring for 0.5 hour at room temperature. To the reaction solution was dropwise added a solution prepared by dissolving 364 mg (2.2 mmol) of phenylpyruvic acid into 4 ml of methanol, and 1.2 ml (8.9 mmol) of triethylamine was furthermore dropwise added thereto. The bath was heated up to a temperature of 40° C., and then 0.25 ml (6.7 mmol) of formic acid was dropwise added over 1 hour, followed by stirring for 2 hours at a bath temperature of 40° C. Upon completion of the reaction, the solvent was distilled off under reduced pressure. Thereto was added 2 ml of water, and then concentrated hydrochloric acid was gradually dropwise added under ice cooling; thus, pH of the solution was adjusted to 2. Extraction was performed twice with 20 ml of ethyl acetate, and then the organic phase was washed with 2 ml of a saturated aqueous solution of sodium chloride, followed by concentration under reduced pressure. As a result, 370 mg (yield 99%, 94% ee) of (2R)-hydroxy-3-phenylpropanoic acid was obtained.

Workup

  1. customto prepare a solution
  2. additionTo the reaction solution was dropwise added a solution
  3. customprepared
  4. additionwas furthermore dropwise added
  5. temperatureThe bath was heated up to a temperature of 40° C.
  6. stirringby stirring for 2 hours at a bath temperature of 40° C
  7. customUpon completion of the reaction
  8. distillationthe solvent was distilled off under reduced pressure
  9. additionThereto was added 2 ml of water
  10. additionconcentrated hydrochloric acid was gradually dropwise added under ice cooling
  11. extractionExtraction
  12. washthe organic phase was washed with 2 ml of a saturated aqueous solution of sodium chloride
  13. concentrationfollowed by concentration under reduced pressure

Sources & evidence

ORD record
ord-59196f6263b245bc8ca9dd651f95a049
Source dataset
uspto-grants-2011_11
Patent number
US08058471B2

Reaction notes

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