Citric Acid → HCID 10965692, compound

HRID 1884592Notes

Reaction equation

HRID 1884592 reaction equation
C([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C@@H:10]1[O:12][CH2:11]1)=[O:7])(C)(C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C>[OH:12][CH2:11][C@@H:10]1[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 311Citric AcidHCID 9903372(2S,3S)-(-)-3-tert-Butoxycarbonylamino-1,2-epoxy-4-phenylbutane

Product 1

HCID 10965692HCID 10965692, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethanol (27.5 ml) was added to (2S, 3S)-3-tert-butoxycarbonylamino-1,2-epoxy-4-phenylbutane (2.75 g), followed by addition of aqueous 6.8% citric acid solution (29.5 g) and agitation at 70° C. for 2 hours. After cooling to ambient temperature, ethanol was removed under reduced pressure. The product was extracted by using ethyl acetate, followed by drying over anhydrous sodium sulfate and concentration under reduced pressure. Furthermore, a mixture solvent of hexane (2.5 ml) and ethyl acetate (2.5 ml) was added, to generate crystal. The crystal was filtered, and then, the crystal was rinsed twice by using a mixture solvent of hexane/ethyl acetate (1/1). The resulting crystal was dried, to afford the objective (4S, 5R)-5-hydroxymethyl-4-phenylmethyloxazolidin-2-one (1.79 g) in 80% yield.

Workup

  1. customethanol was removed under reduced pressure
  2. extractionThe product was extracted
  3. dry with materialby drying over anhydrous sodium sulfate and concentration under reduced pressure
  4. additionFurthermore, a mixture solvent of hexane (2.5 ml) and ethyl acetate (2.5 ml) was added
  5. filtrationThe crystal was filtered
  6. washthe crystal was rinsed twice
  7. customThe resulting crystal was dried

Sources & evidence

ORD record
ord-0035ecca53f140bb8a37d56d8414f4b7
Source dataset
uspto-grants-2004_07
Patent number
US06765100B2

Reaction notes

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