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

HRID 567148Notes

Reaction equation

HRID 567148 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 for 3 hours at this temperature and then, after returning to room temperature, ethyl acetate is added, separation is carried out by settling, the aqueous phase is acidified with a 1N aqueous hydrochloric acid solution, extracted with ethyl acetate, 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, filtered off and dried. There is obtained 0.4 g of (S)-2-(2-methoxyphenyl)propionic acid 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. customseparation
  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 recrystallized from hexane
  8. filtrationfiltered off
  9. customdried

Sources & evidence

ORD record
ord-0619359944a541fa81caad3f7e9784d8
Source dataset
uspto-grants-2001_01
Patent number
US06177450B1

Reaction notes

Loading…