Sulfuric Acid → (4S,5S)-5-hydroxymethyl-4-phenylmethyloxazolidinone

HRID 1600356Notes

Reaction equation

HRID 1600356 reaction equation
[CH2:1]([C@H:8]1[C@@H:12]([C:13](O)=[O:14])[O:11][C:10](=[O:16])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[OH-].[Na+]>C(O)C>[CH2:1]([C@H:8]1[C@@H:12]([CH2:13][OH:14])[O:11][C:10](=[O:16])[NH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 14558093(4S,5S)-2-Oxo-4-(phenylmethyl)-5-oxazolidinecarboxylic acid

Product 1

HCID 9859125(4S,5S)-5-hydroxymethyl-4-phenylmethyloxazolidinone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

1.1 g (5 mmol) of (4S,5S)-4-benzyl-oxazolidin-2-one-5-carboxylic acid were dissolved in 15 ml of ethanol. 0.03 ml of sulphuric acid were added and the mixture refluxed for 4 hours. After cooling, 0.04 g of NaOH were addedand the mixture concentrated under a vacuum to 2 g. 4 ml of ethanol were then added and 0.25 g of NaBH4 was added in small portions. Once addition was complete and stirring had been continued for 0.5 hour, the educt was already completely converted. 4 ml of water were added, the mixture neutralised to pH 7 with 1.2 ml of 10% HCl and, after cooling, cooled to 0° C. The solid was separated using a vacuum filter and, due to the small batch size, washed with a disproportionately large quantity of water. The yield after isolation was 0.66 g=63.7%, wherein approximately 0.2 g=20% of theoretical still remained in the mother liquorand washing water. Diastereomer purity was S,S:R,S=98.75:1.

Workup

  1. temperaturethe mixture refluxed for 4 hours
  2. temperatureAfter cooling
  3. concentrationconcentrated under a vacuum to 2 g
  4. addition4 ml of ethanol were then added
  5. addition0.25 g of NaBH4 was added in small portions
  6. additionOnce addition
  7. addition4 ml of water were added
  8. temperatureafter cooling
  9. customThe solid was separated
  10. filtrationfilter and, due to the small batch size
  11. washwashed with a disproportionately large quantity of water
  12. customThe yield after isolation
  13. washliquorand washing water

Sources & evidence

ORD record
ord-d5248699d0164c9fb6abac47b9a8e61f
Source dataset
uspto-grants-1998_04
Patent number
US05744611

Reaction notes

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