Citric Acid → HCID 10965692, compound

HRID 393398Notes

Reaction equation

HRID 393398 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>[CH2:13]([C@H:9]1[C@H:10]([CH2:11][OH:12])[O:5][C:6](=[O:7])[NH:8]1)[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 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To (2S,3S)-3-tert-butoxycarbonylamino-1,2-epoxy-4-phenylbutane obtained in the same manner as in Reference Example 2 (2.75 g) was added ethanol (27.5 ml). 6.8% Aqueous citric acid solution (29.5 g) was then added thereto, and the mixture was stirred at 70° C. for 2 hr. After cooling to room temperature, ethanol was removed under reduced pressure. The residue was extracted with ethyl acetate, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Further, a mixed solvent of hexane (2.5 ml) and ethyl acetate (2.5 ml) was added to allow precipitation of the crystals. The crystals were collected by filtration and washed twice with a mixed solvent of hexane/ethyl acetate (1/1). The obtained crystals were dried to give the objective (4S,5R)-4-benzyl-5-hydroxymethyloxazolidin-2-one (1.79 g) in a yield of 80%.

Workup

  1. temperatureAfter cooling to room temperature
  2. customethanol was removed under reduced pressure
  3. extractionThe residue was extracted with ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionFurther, a mixed solvent of hexane (2.5 ml) and ethyl acetate (2.5 ml) was added
  7. customprecipitation of the crystals
  8. filtrationThe crystals were collected by filtration
  9. washwashed twice with a mixed solvent of hexane/ethyl acetate (1/1)
  10. customThe obtained crystals were dried

Sources & evidence

ORD record
ord-ff46a0c381984ace95102ac73e0a5840
Source dataset
uspto-grants-2004_10
Patent number
US06806384B2

Reaction notes

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