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

HRID 2400006Notes

Reaction equation

HRID 2400006 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]-2-oxazolidinone in 60 cm3 of tetrahydrofuran and 30 cm3 of water. The reaction mixture is stirred for 3 hours at this temperature and then, after re-equilibrating to room temperature, ethyl acetate is added, the mixture is decanted and the aqueous phase is acidified with a 1N aqueous solution of hydrochloric acid, 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 point 102° C. [α]D20 =+84.6° (c=1; CHCl3).

Workup

  1. customthe mixture is decanted
  2. extractionextracted with ethyl acetate
  3. dry with materialthe organic phase is dried over magnesium sulphate
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  5. customThe solid obtained
  6. customis recrystallized from hexane
  7. customdried

Sources & evidence

ORD record
ord-5ce04d39bf3744d386c91160d8ade0bc
Source dataset
uspto-grants-1995_09
Patent number
US05451601

Reaction notes

Loading…