HCID 73743102, compound → HCID 72451686, compound

HRID 643249Notes

Reaction equation

HRID 643249 reaction equation
[C:1]([O:9][N:10]=[C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:12]1[CH2:16][CH2:15][CH2:14][N:13]1C(OC(C)(C)C)=O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>FC(F)(F)C(O)=O.ClCCl>[CH2:1]([O:9][N:10]=[C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:12]1[CH2:16][CH2:15][CH2:14][NH:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 73743102HCID 73743102, compound

Product 1

HCID 72451686HCID 72451686, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

8 g (20 mmol) of tert-butyl 2-[[(benzoyloxy)imino](phenyl)methyl]-1-pyrrolidinecarboxylate dissolved in 400 ml of a mixture of 30% trifluoroacetic acid in dichloromethane are introduced into a 500 ml round-bottomed flask equipped with a magnetic stirrer, and the mixture is stirred for 4 hours at room temperature. After evaporating the reaction medium to dryness under reduced pressure, the residue is diluted with aqueous ammonia and dichloromethane, and the aqueous phase is separated out and extracted with dichloromethane. After washing the combined organic phases, drying over sodium sulfate and evaporating the solvent under reduced pressure, the residue is purified by column chromatography on silica gel, eluting with a mixture of dichloromethane and methanol.

Workup

  1. additionare introduced into a 500 ml round-bottomed flask
  2. customequipped with a magnetic stirrer
  3. customAfter evaporating the reaction medium to dryness under reduced pressure
  4. additionthe residue is diluted with aqueous ammonia and dichloromethane
  5. customthe aqueous phase is separated out
  6. extractionextracted with dichloromethane
  7. washAfter washing the combined organic phases
  8. dry with materialdrying over sodium sulfate
  9. customevaporating the solvent under reduced pressure
  10. customthe residue is purified by column chromatography on silica gel
  11. washeluting with a mixture of dichloromethane and methanol

Sources & evidence

ORD record
ord-c1fd2d9428a04863b06ed8eaf8f1b849
Source dataset
uspto-grants-2010_04
Patent number
US07700585B2

Reaction notes

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