Formaldehyde → (S)-N-Cbz-4-methyl-5-oxooxazolidine

HRID 1795480Notes

Reaction equation

HRID 1795480 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:14]([OH:16])=[O:15])[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]=O>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:1]([O:8][C:9]([N:11]1[C@@H:12]([CH3:13])[C:14](=[O:16])[O:15][CH2:17]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 736104N-carbobenzyloxyalanine

Product 1

HCID 355115(S)-N-Cbz-4-methyl-5-oxooxazolidineYield 93.4%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

Benzyloxycarbonyl-L-alanine (19.3 g), paraformaldehyde (6.56 g) and p-toluenesulfonic acid monohydrate (0.17 g) were suspended in toluene (190 mL), and the mixture was heated at reflux while removing water produced. At the end of the reaction, the reaction mixture was cooled to room temperature, washed with saturated aqueous sodium hydrogen carbonate solution and then saturated saline. The toluene solution was dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure, the resulting crystals were filtrated to give the title compound (19.0 g) as white crystals in an yield of 93%.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux
  3. customwhile removing water
  4. customproduced
  5. customAt the end of the reaction
  6. washwashed with saturated aqueous sodium hydrogen carbonate solution
  7. dry with materialThe toluene solution was dried over anhydrous sodium sulfate
  8. customThe solvent was evaporated under a reduced pressure
  9. filtrationthe resulting crystals were filtrated

Sources & evidence

ORD record
ord-e2c0605219b84bff843bba75bf0b3354
Source dataset
uspto-grants-2006_04
Patent number
US07026515B2

Reaction notes

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