Propionyl chloride → Propionyl Oxazolidinone

HRID 1030304Notes

Reaction equation

HRID 1030304 reaction equation
[O:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].C([Li])CCC.[C:12](Cl)(=[O:15])[CH2:13][CH3:14]>CCCCCC>[C:12]([N:3]1[CH2:4][CH2:5][O:1][C:2]1=[O:6])(=[O:15])[CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 62324Propionyl chlorideHCID 739492-Oxazolidinone2×HCID 178418339Butyllithium

Product 1

HCID 641554Propionyl Oxazolidinone

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Following the cyclization reaction, the formed oxazolidinone is N-acylated to form the nucleophilic precursor of the molecule. The oxazolidinone is reacted with butyllithium in hexane, to form the conjugate base and then reacted with an acyl halide such as propionyl chloride at -71° C., for 0.5-1 hour to yield the N-propionyloxazolidinone.

Workup

  1. customthe cyclization reaction
  2. customto form the nucleophilic precursor of the molecule
  3. customto form the conjugate base

Sources & evidence

ORD record
ord-b3cebe68593d44d491ec79a878754b0f
Source dataset
uspto-grants-1992_04
Patent number
US05104984

Reaction notes

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