Hydrogen Peroxide → HCID 13987528, compound

HRID 1780966Notes

Reaction equation

HRID 1780966 reaction equation
C[C@@H]1[C@@H](C2C=CC=CC=2)OC(=O)N1[C:14](=[O:25])[C@@H:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][CH3:24])[CH3:16].[OH-].[Li+].OO.S([O-])([O-])=[O:31].[Na+].[Na+]>O1CCCC1.O>[CH3:24][O:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C@@H:15]([CH3:16])[C:14]([OH:25])=[O:31]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 24437Sodium SulfiteHCID 57271238HCID 57271238, compound

Product 1

HCID 13987528HCID 13987528, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution, cooled to +5° C., of 10.88 g of (4R, 5R)-4-methyl-5-phenyl-3-[(R)-2-(2-methoxyphenyl)propionyl]-2-oxazolidinone in 300 cm3 of tetrahydrofuran and 100 cm3 of water are added 2.71 g of lithium hydroxide and 13 cm3 of aqueous 30% hydrogen peroxide solution. The reaction mixture is stirred for 3 hours at this temperature, followed, after returning to room temperature, by addition of aqueous sodium sulphite solution and then dichloromethane, and the phases are separated after settling. The aqueous phase is acidified with 4N aqueous hydrochloric acid solution and extracted with dichloromethane, and the organic phase is then dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The solid obtained is recrystallized in hexane, filtered off and dried. 5.24 g of (R)-2-(2-methoxyphenyl)propionic acid are obtained, in the form of white crystals melting at 102° C.; [α]D20 =-76° (c=1; methanol).

Workup

  1. customdichloromethane, and the phases are separated
  2. extractionextracted with dichloromethane
  3. dry with materialthe organic phase is then dried over magnesium sulphate
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  5. customThe solid obtained
  6. customis recrystallized in hexane
  7. filtrationfiltered off
  8. customdried

Sources & evidence

ORD record
ord-333a9cb6f4c44addbf85a8788cba6880
Source dataset
uspto-grants-1997_05
Patent number
US05631279

Reaction notes

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