Benzene → 2-Oxazolidinone

HRID 403008Notes

Reaction equation

HRID 403008 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:34]([OH:36])=[O:35])CC1C(I)=CC(OC(OC(C)(C)C)=O)=C(OC(OC(C)(C)C)=O)C=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:37]12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.C=O.C1C=CC=CC=1>C(OCC)(=O)C>[O:36]1[CH2:34][CH2:9][NH:8][C:6]1=[O:7].[C:1]([O:5][C:6]([N:8]1[CH2:9][C:34](=[O:35])[O:36][CH2:37]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 241BenzeneHCID 712FormaldehydeHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 66733684N-(tert-butoxycarbonyl)-3,4-di(tert-butoxycarbonyloxy)-6-iodo-L-phenylalanine

Product 2

HCID 739492-OxazolidinoneHCID 20628126tert-Butyl 5-oxooxazolidine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the iodo amino acid 23 (0.86 mmol), camphorsulfonic acid (0.17 mmol), paraformaldehyde (1.29 mmol) and benzene (10 mL) was refluxed for 2 h. The mixture was diluted with ethyl acetate and was washed with 5% aqueous sodium bicarbonate solution. The organic phase was dried with anhydrous sodium sulfate, filtered and purified by silica gel column chromatography using 40% EtOAc/Hexane mixture as eluent to obtain pure oxazolidinone product 24 (N-(tert-butoxycarbonyl)-1,3-oxazolidin-5-one derivative) as an oil in 35% yield.

Workup

  1. temperaturewas refluxed for 2 h
  2. washwas washed with 5% aqueous sodium bicarbonate solution
  3. dry with materialThe organic phase was dried with anhydrous sodium sulfate
  4. filtrationfiltered
  5. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-046f4b8558d14af5896e4b4cb541b9be
Source dataset
uspto-grants-2014_06
Patent number
US08742139B2

Reaction notes

Loading…