Lithium Hydroxide → (S)-2-(2-Methoxyphenyl)propanoic acid

HRID 1599130Notes

Reaction equation

HRID 1599130 reaction equation
[OH-].[Li+].C[C@H]1[C@H](C2C=CC=CC=2)OC(=O)N1[C:16](=[O:27])[C@H:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH3:26])[CH3:18].C(OCC)(=[O:30])C>O1CCCC1.O>[CH3:26][O:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C@H:17]([CH3:18])[C:16]([OH:27])=[O:30]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 54310187(4S,5S)-4-methyl5-phenyl-3-[(S)-2-(2-methoxyphenyl)propionyl]2-oxazolidinone

Product 1

HCID 11137716(S)-2-(2-Methoxyphenyl)propanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.52 g of lithium hydroxide are added to a solution, cooled to +5° C., of 4.1 g of (4S,5S)-4-methyl-5-phenyl-3-[(S)-2-(2-methoxyphenyl)propionyl]oxazolidin-2-one in 60 cm3 of tetrahydrofuran and 30 cm3 of water. The reaction mixture is stirred at this temperature for 3 hours and then, after returning to room temperature, ethyl acetate is added, the phases are separated by decanting, the aqueous phase is acidified with 1N aqueous hydrochloric acid solution and extracted with ethyl acetate, and the organic phase is dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The solid obtained is recrystallized from hexane, drained and dried. 0.4 g of (S)-2-(2-methoxyphenyl)propionic acid is obtained in the form of white crystals melting at 102° C. [α]D20 =+84.6° (C=1; CHCl3)

Workup

  1. customafter returning to room temperature
  2. customthe phases are separated
  3. customby decanting
  4. extractionextracted with ethyl acetate
  5. dry with materialthe organic phase is dried over magnesium sulphate
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  7. customThe solid obtained
  8. customis recrystallized from hexane
  9. customdried

Sources & evidence

ORD record
ord-da768ae6e9dd4008bb3183c3237086dd
Source dataset
uspto-grants-1998_04
Patent number
US05739351

Reaction notes

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