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

HRID 2211402Notes

Reaction equation

HRID 2211402 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-[2-(2-methoxyphenyl)-(S)-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, after returning to room temperature, ethyl acetate is added, the mixture is decanted, the aqueous phase is acidified with an aqueous 1N solution of hydrochloric acid 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 recrystallised from hexane, filtered off and dried. 0.4 g of (S)-2-(2-methoxyphenyl)-propionic acid is obtained in the form of white crystals which melt at 102° C. [α]D20 =+84.6° (c=1; CHCl3).

Workup

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

Sources & evidence

ORD record
ord-0007f87a200f4b12aeb72cb99581af7d
Source dataset
uspto-grants-1995_10
Patent number
US05463077

Reaction notes

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